@article { ISI:000325642400017, title = {Electrophile induced branching cascade: a powerful approach to access various molecular scaffolds and their exploration as novel anti-mycobacterial agents}, journal = {Chemical Communications}, volume = {49}, number = {86}, year = {2013}, month = {SEP}, pages = {10109-10111}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Herein we report on the Electrophile Induced Branching Cascade (EIBC), a new technique to produce a variety of biologically important molecular scaffolds. Some compounds exhibit excellent activities against Mycobacterium smegmatis.

}, issn = {1359-7345}, doi = {10.1039/c3cc45289a}, author = {Patil, Nitin T. and Konala, Ashok and Sravanti, Sudha and Singh, Ashita and Ummanni, Ramesh and Sridhar, Balasubramanian} } @article {42863, title = {Relay catalytic branching cascade: technique to access diverse molecular scaffolds}, journal = {Angewandte Chemie International Edition}, volume = {52}, year = {2013}, month = {JAN}, pages = {2251-2255}, doi = {10.1002/anie.201208738}, author = {Patil, Nitin T. and Shinde, Valmik S. and Sridhar, Balasubramanian} } @article { ISI:000364426500019, title = {Enantioselective heterogeneous bronsted acid catalysis}, journal = {Organic Chemistry Frontiers}, volume = {1}, number = {5}, year = {2014}, month = {MAR}, pages = {582-586}, publisher = {CHINESE CHEMICAL SOC}, address = {PO BOX 1-18, NANKANG, TAIPEI 115, TAIWAN}, abstract = {

This highlight describes the synthesis and catalytic activities of heterogeneous chiral Bronsted acid catalysts. The heterogeneous catalysts are stable, easily separable from the reaction mixture and can be used multiple times without any loss of activity. As a remarkable particularity, the use of heterogeneous catalyst systems has been exemplified for designing continuous flow reactors.

}, issn = {2052-4129}, doi = {10.1039/c4qo00051j}, author = {Mutyala, Anil Kumar and Patil, Nitin T.} } @article { ISI:000344997100001, title = {When gold meets chiral bronsted acid catalysts: extending the boundaries of enantioselective gold catalysis}, journal = {Chemical Communications}, volume = {50}, number = {96}, year = {2014}, month = {AUG}, pages = {15124-15135}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

This review describes the development in the use of Au(I)/Bronsted acid binary catalytic systems to enable an enantioselective transformation in one-pot that cannot be achieved by gold catalysts alone. The examples discussed herein are promising since apart from using chiral ligands there exists a possibility of using chiral Bronsted acids. Clearly, the horizon for enantioselective gold catalysis has been expanded as more options to make the gold-catalyzed reactions enantioselective have become available.

}, issn = {1359-7345}, doi = {10.1039/c4cc04633a}, author = {Inamdar, Suleman M. and Konala, Ashok and Patil, Nitin T.} } @article { ISI:000348510400004, title = {Catalyst-dependent selectivity in the relay catalytic branching cascade}, journal = {Chemistry-A European Journal}, volume = {21}, number = {6}, year = {2015}, month = {FEB}, pages = {2319-2323}, publisher = {WILEY-V C H VERLAG GMBH}, address = {BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY}, abstract = {

The synthesis of small organic molecules as probes for discovering new therapeutic agents has been an important aspect of chemical biology. One of the best ways to access collections of small molecules is to use various techniques in diversity-oriented synthesis (DOS). Recently, a new form of DOS, namely relay catalytic branching cascades (RCBCs), has been introduced, wherein a common type of starting material reacts with several scaffold-building agents (SBAs) to obtain structurally diverse molecular scaffolds under the influence of catalysts. Herein, the RCBC reaction of a common type of substrate with SBAs is reported to give two different types of molecular scaffolds and their formation is essentially dependent on the type of catalyst used.

}, keywords = {alkynols, cascade synthesis, chemoselectivity, diversity-oriented synthesis, Homogeneous catalysis}, issn = {0947-6539}, doi = {10.1002/chem.201405736}, author = {Bansode, Avinash H. and Shaikh, Aslam C. and Kavthe, Rahul D. and Thorat, Shridhar and Gonnade, Rajesh G. and Patil, Nitin T.} } @article { ISI:000358349700002, title = {Enantioselective cooperative catalysis}, journal = {Organic \& Biomolecular Chemistry}, volume = {13}, number = {30}, year = {2015}, month = {JUN}, pages = {8116-8162}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

In recent years, enantioselective cooperative catalytic reactions, wherein two catalysts work simultaneously to form products which cannot be obtained by the use of a single catalyst alone, have attracted considerable attention. This review focuses on this emerging field, with particular emphasis on mechanistic aspects, which will help readers to understand the role of each catalyst.

}, issn = {1477-0520}, doi = {10.1039/c5ob00986c}, author = {Inamdar, Suleman M. and Shinde, Valmik S. and Patil, Nitin T.} } @article { ISI:000364449200020, title = {Engineering ligands on the Au center: discovering broadly applicable gold catalysis with high turnover numbers}, journal = {Organic Chemistry Frontiers}, volume = {2}, number = {8}, year = {2015}, month = {JUN}, pages = {995-998}, publisher = {CHINESE CHEMICAL SOC}, address = {PO BOX 1-18, NANKANG, TAIPEI 115, TAIWAN}, abstract = {

The research groups of Hammond/Xu and Zhang report the discovery of new ligands for gold catalysis. With these ligands, gold catalyzed reactions have been reported for a broader range of substrates with very high TONs at a level that can match the needs of large-scale applications.

}, issn = {2052-4129}, doi = {10.1039/c5qo00162e}, author = {Inamdar, Suleman M. and Patil, Nitin T.} } @article {42859, title = {Gold(I)/chiral br{\o}nsted acid catalyzed enantioselective hydroamination-hydroarylation of alkynes: effect of remote hydroxyl group in the reactivity and enantioselectivity}, journal = {Chemistry - A European Journal}, volume = {21}, year = {2015}, month = {JAN}, pages = {975-979}, doi = {10.1002/chem.201405061}, author = {Shinde, Valmik S. and Mane, Manoj V. and Vanka, Kumar and Mallick, Arijit and Patil, Nitin T.} } @article { ISI:000363666000023, title = {Highly emissive organic solids with remarkably broad color tunability based on N,C-chelate, four-coordinate organoborons}, journal = {Chemical Communications}, volume = {51}, number = {89}, year = {2015}, month = {SEP}, pages = {16115-16118}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Molecular fluorophores based on N,C-chelate, four-coordinate organo-borons exhibit tunable solid-state emission colors that cover the whole visible region from blue to red. The emission color can be tuned through the substituents on either quinolines or the boron center.

}, issn = {1359-7345}, doi = {10.1039/c5cc06351e}, author = {Shaikh, Aslam C. and Ranade, Dnyanesh S. and Thorat, Shridhar and Maity, Arunava and Kulkarni, Prasad P. and Gonnade, Rajesh G. and Munshi, Parthapratim and Patil, Nitin T.} } @article { ISI:000358370700007, title = {Identifying solid luminogens through gold-catalysed intramolecular hydroarylation of alkynes}, journal = {European Journal of Organic Chemistry}, number = {22}, year = {2015}, month = {AUG}, pages = {4860-4867}, publisher = {WILEY-V C H VERLAG GMBH}, address = {POSTFACH 101161, 69451 WEINHEIM, GERMANY}, abstract = {

The identification of a new class of luminogens based on pyrrolo-quinoxaline embedded coumarin (PQC) structures is reported. The reaction relies on the gold-catalyzed hydroarylation reaction of appropriately substituted aryl alkynoates that produces molecules that exhibit solvatochromism and aggregation-induced emission enhancement (AIEE) phenomena. The application of PQCs for live cell imaging has also been demonstrated.

}, keywords = {Cell imaging, Dyes/pigments, fluorescence, Gold, Luminescence, Solvatochromism}, issn = {1434-193X}, doi = {10.1002/ejoc.201500503}, author = {Shaikh, Aslam C. and Shalini, S. and Vaidhyanathan, Ramanathan and Mane, Manoj V. and Barui, Ayan Kumar and Patra, Chitta Ranjan and Venkatesh, Yeduru and Bangal, Prakriti Ranjan and Patil, Nitin T.} } @article { ISI:000350116200014, title = {Robustness screen in enantioselective catalysis enabled generation of enantioenriched heterocyclic scaffolds in one pot}, journal = {Chemistry-A European Journal}, volume = {21}, number = {9}, year = {2015}, month = {FEB}, pages = {3580-3584}, publisher = {WILEY-V C H VERLAG GMBH}, address = {BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY}, abstract = {

Enantioselective catalysis has emerged as a powerful synthetic paradigm and has accelerated the development of new methods to make diverse chiral molecules. Generally, these reactions are very sensitive to the steric and electronic environment present in the catalyst as well as the substrates. With this scenario, the presence of an additional component in the reaction mixture is expected to add complexity in achieving the enantioselective variants. Herein, we report that various enantioenriched molecules could be obtained from multiple starting materials in one pot. The reaction of aminoaromatics A with alkynols B-1, B-2, B-3...B-n with a Au-I/chiral BrOnsted acid catalyst afforded AB(1)*, AB(2)*, AB(3)*...AB(n)*; while, the reaction of alkynols B with aminoaromatics A(1), A(2), A(3)...A(n) under the same reaction conditions gave A(1)B*, A(2)B*, A(3)B*...A(n)B*.

}, keywords = {chiral Bronsted acid, Enantioselectivity, Gold, molecular scaffolds, robustness screen}, issn = {0947-6539}, doi = {10.1002/chem.201406045}, author = {Bagle, Pradip N. and Shinde, Valmik S. and Patil, Nitin T.} } @article {42844, title = {Au(I)/Ag(I) co-operative catalysis: interception of Ag-bound carbocations with α-gold(I) enals in the imino-alkyne cyclizations with N-allenamides}, journal = {Chemical Communications}, volume = {52}, year = {2016}, month = {NOV}, pages = {14462-14465}, doi = {10.1039/C6CC08385D}, author = {Bagle, Pradip N. and Mane, Manoj V. and Vanka, Kumar and Shinde, Dinesh R. and Shaikh, Samir R. and Gonnade, Rajesh G. and Patil, Nitin T.} } @article { ISI:000378390300022, title = {Efficient access to alkynylated quinalizinones via the gold(I)-catalyzed aminoalkynylation of alkynes}, journal = {Chemical Communications}, volume = {52}, number = {52}, year = {2016}, month = {MAY}, pages = {8152-8155}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

The gold-catalyzed aminoalkynylation of alkynes for the synthesis of quinalizinones is reported. For instance, the reaction of pyridinoalkynes with 1-[(triisopropylsilyl)-ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) in the presence of a catalytic amount of AuCl at 50 8C afforded alkynylated quinalizinones in 57-87\% yields.

}, issn = {1359-7345}, doi = {10.1039/c6cc03414d}, author = {Shinde, Popat S. and Shaikh, Aslam C. and Patil, Nitin T.} } @article {42847, title = {Facile strategy for accessing 3-alkynylchromones through gold-catalyzed alkynylation/cyclization of o-hydroxyarylenaminones}, journal = {Chemical Communications}, volume = {52}, year = {2016}, month = {SEP}, pages = {12306-12309}, abstract = {

A strategy based on tandem alkynylation of o-hydroxyarylenaminones followed by intramolecular cyclization has been developed to generate a diverse array of 3-alkynyl chromones. The functionality embedded in these key intermediates enables their facile elaboration into more diverse structures by a variety of functionalizations and ring-forming processes.

}, doi = {10.1039/C6CC07119H}, author = {Akram, Manjur O. and Bera, Saibal and Patil, Nitin T.} } @article { ISI:000371754000043, title = {Gold vs rhodium catalysis: tuning reactivity through catalyst control in the C-H alkynylation of isoquinolones}, journal = {Organic Letters}, volume = {18}, number = {5}, year = {2016}, month = {MAR}, pages = {1056-1059}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

A site-selective C-4/C-8 alkynylation of isoquinolones catalyzed by gold and rhodium complexes is reported. A broad range of synthetically useful functional groups (-F, -Cl, -Br, -CF3, -OMe, alkyl, etc.) were tolerated, providing an efficient and robust protocol for the synthesis either C-4- or C-8-alkynylated isoquinolones.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.6b00175}, author = {Shaikh, Aslam C. and Shinde, Dinesh R. and Patil, Nitin T.} } @article { ISI:000374436800034, title = {Gold(I)-catalyzed hydroaminaloxylation and petasis-ferrier rearrangement cascade of aminaloalkynes}, journal = {Organic Letters}, volume = {18}, number = {8}, year = {2016}, month = {APR}, pages = {1844-1847}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

An efficient method has been developed to generate a diverse array of indolizidines and quinolizidines from readily available aminaloalkynes via a gold(I)-catalyzed hydroaminaloxylation and Petasis-Ferrier rearrangement cascade. The method enabled a formal synthesis of (+/-)-antofine.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.6b00585}, author = {Gade, Amol B. and Patil, Nitin T.} } @article {42843, title = {Oxidative intramolecular 1,2-amino-oxygenation of alkynes under Au(I)/Au(III)-catalysis: discovery of pyridinium-oxazole dyad as novel lonic fluorophore}, journal = {Angewandte Chemie International Edition}, year = {2016}, month = {JAN}, doi = {10.1002/anie.201609335R1}, author = {Shaikh, Aslam C. and Ranade, Dnyanesh S. and Rajamohanan, Pattuparambil R. and Kulkarni, Prasad P. and Patil, Nitin T.} } @article { ISI:000377612300015, title = {Scandium triflate catalyzed unexpected cleavage of C-C bonds in ynones}, journal = {Arkivoc}, number = {2}, year = {2016}, month = {NOV}, pages = {223-232}, publisher = {ARKAT USA INC}, address = {C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA}, abstract = {

An unexpected C-C bond cleavage in ynones in the presence of catalytic amounts of Sc(OTf)(3) in methanol under microwave irradiation has been discussed. The effect of substituent on the regioselectivity of C-C bond cleavage has carefully been addressed by employing various ynones derivatives. The mechanism has been proposed for the observed regioselectivity.

}, keywords = {C-C bond cleavage, Esters, Ketones, scandium triflate, ynones}, issn = {1551-7004}, doi = {10.3998/ark.5550190.p009.244}, author = {Kavthe, Rahul D. and Bansode, Avinash H. and Patil, Nitin T.} } @article { ISI:000374049700040, title = {Unified approach to pyrrole-embedded aza-heterocyclic scaffolds based on the RCM/isomerization/cyclization cascade catalyzed by a Ru/B-H binary catalyst system}, journal = {RSC Advances}, volume = {6}, number = {41}, year = {2016}, month = {MAR}, pages = {34428-34433}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

An easy and straightforward preparation of pyrrole-embedded aza-heterocyclic scaffolds employing a Ru/B-H binary catalyst system has been developed. The strategy generates a diverse array of privileged scaffolds from 2-aminophenyl group appended pyrroles that can be prepared by a two-step process from corresponding aminoaryl-substituted pyrroles. The technique of incorporating 2-aminoaromatic groups in the heterocycles and their subsequent ring-closing-metathesis (RCM) isomerization followed by subsequent Pictet-Spengler type reaction should also be applicable to other heterocycles for generating a library of multi-ring compounds in an efficient manner.

}, issn = {2046-2069}, doi = {10.1039/c6ra05646f}, author = {Inamdar, Suleman M. and Chakrabarty, Indradweep and Patil, Nitin T.} } @article {42825, title = {[3+2]-Annulation of platinum-bound azomethine ylides with distal C[double bond, length as m-dash]C bonds of N-allenamides}, journal = {Chemical Communications}, volume = {53}, year = {2017}, month = {JAN}, pages = {196-199}, type = {Article}, abstract = {

A Pt-catalyzed, highly regioselective reaction between N-allenamides and imino-alkynes leading to pyrrolo[1,2-a] indoles is described. This represents the first example of [3+2]-annulation of Pt-bound azomethine ylides with the distal CQC bond of N-allenamides. The mechanism of the reaction was established by computational studies.

}, doi = {10.1039/c6cc07874e}, author = {Chakrabarty, Indradweep and Inamdar, Suleman M. and Akram, Manjur O. and Gade, Amol B. and Banerjee, Subhrashis and Bera, Saibal and Patil, Nitin T.} } @article {42850, title = {Catalytic branching cascades in diversity oriented synthesis}, journal = {ChemCatChem}, volume = {9}, year = {2017}, month = {OCT}, pages = { 30-40}, type = {Article}, abstract = {

Diversity oriented synthesis (DOS) aims to generate small molecules with great structural diversity in an efficient manner. Recent years have witnessed significant achievements in the field, which help to validate the usefulness of DOS as a tool for the discovery of novel, biologically interesting small molecules. Catalytic branching cascades have emerged as a promising strategy because of their potential to transform a common type of substrate into diverse and distinct molecular frameworks. The details of the concept are presented herein.

}, doi = {10.1002/cctc.201600766}, author = {Bansode, Avinash H. and Chimala, Prathyusha and Patil, Nitin T.} } @article {43359, title = {Catalytic enantioselective aza-piancatelli rearrangement}, journal = {Synlett}, volume = {28}, year = {2017}, month = {JUN}, pages = {1096-1100}, type = {Article}, abstract = {The design and development of an enantioselective aza-Piancatelli rearrangement reaction are described. In the presence of a chiral phosphoric acid catalyst, furylcarbinols react with anilines to afford highly functionalized cyclopentenones with excellent diastereo-and enantioselectivities. The process was shown to be scalable, and up to 1 gram of starting material could be employed under mild reaction conditions.}, doi = {10.1055/s-0036-1558952}, author = {Gade, Amol B. and Patil, Nitin T.} } @article {43877, title = {Cross-coupling reactions of aryldiazonium salts with allylsilanes under merged gold/visible-light photoredox catalysis}, journal = {Organic Letters}, volume = {19}, year = {2017}, month = {JUN}, pages = {3075-3078}, type = {Article}, abstract = {A method for the cross-coupling reactions of aryldiazonium salts with trialkylallylsilanes via merged gold/photoredox catalysis is described. The reaction is proposed to proceed through a photoredox-promoted generation of an electrophilic arylgold(III) intermediate that undergoes transmetalation with allyltrimethylsilane to form allylarenes.}, doi = {10.1021/acs.orglett.7b01148}, author = {Akram, Manjur O. and Mali, Pramod S. and Patil, Nitin T.} } @article {43842, title = {Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)-C(sp) cross-coupling reactions}, journal = {Chemical Communications}, volume = {53}, year = {2017}, month = {JUL}, pages = {7937-7940}, type = {Article}, abstract = {Reported herein is the gold-catalyzed alkynylation of terminal alkynes using ethynylbenziodoxolones (EBXs), where EBXs serve a dual role as oxidants as well as alkyne transfer agents to access unsymmetrical 1,3-diynes. Hence, the catalytic system requires no external oxidants and is compatible with a broad range of substrates, including those with polar functional groups such as NH, OHand B(OH)(2).}, doi = {10.1039/c7cc04283c}, author = {Banerjee, Somsuvra and Patil, Nitin T.} } @article {43867, title = {Gold-catalyzed dehydrazinative C(sp)-S coupling reactions of arylsulfonyl hydrazides with ethynylbenziodoxolones for accessing alkynyl sulfones}, journal = {European Journal of Organic Chemistry}, year = {2017}, month = {JUN}, pages = {3512-3515}, type = {Article}, abstract = {A gold(III)-catalyzed dehydrazinative coupling reaction between arylsulfonyl hydrazides and ethynylbenziodoxolone reagents was realized for the synthesis of alkynyl sulfones. The scope and versatility of the reaction were demonstrated by the efficient synthesis of 23 derivatives with diverse structural features.}, doi = {10.1002/ejoc.201700524}, author = {Shinde, Popat S. and Patil, Nitin T.} } @article {43797, title = {Intramolecular ipso-arylative cyclization of aryl-alkynoates and N-arylpropiolamides with aryldiazonium salts through merged gold/visible light photoredox catalysis}, journal = {Chemical Communications}, volume = {53}, year = {2017}, month = {AUG}, pages = {9081-9084}, type = {Article}, abstract = {A visible-light-promoted merged gold/photoredox catalyzed ipsoarylative cyclization has been reported. For instance, the reaction of aryl-alkynoates and N-arylpropiolamides with aryldiazonium salts in the presence of catalytic amounts of [(4-OCH3)C6H4](3)PAuCl and Ru(bpy)(3)(PF6)(2) under irradiation using a 32WCFL bulb gave arylated spirocarbocycles in moderate to good yields.}, doi = {10.1039/c7cc04010e}, author = {Bansode, Avinash H. and Shaikh, Samir R. and Gonnade, Rajesh G. and Patil, Nitin T.} } @article {43360, title = {Oxidative intramolecular 1,2-amino-oxygenation of alkynes under Au I /Au III catalysis: discovery of a pyridinium-oxazole dyad as an ionic fluorophore}, journal = {Angewandte Chemie-International Edition}, volume = {56}, year = {2017}, month = {JAN}, pages = {757 - 761}, doi = {10.1002/ange.201609335}, author = {Shaikh, Aslam C. and Ranade, Dnyanesh Sadanand and Rajamohanan, Pattuparambil R. and Kulkarni, Prasad Padmakar and Patil, Nitin T.} } @article {43482, title = {Oxidative intramolecular 1,2-amino-oxygenation of alkynes under Au-I/Au-III catalysis: discovery of a pyridinium-oxazole dyad as an ionic fluorophore}, journal = {Angewandte Chemie-International Edition}, volume = {56}, year = {2017}, month = {JAN}, pages = {757-761}, abstract = {Oxidative intramolecular 1,2-amino-oxygenation reactions, combining gold(I)/gold(III) catalysis, is reported. The reaction provides efficient access to a structurally unique ionic pyridinium-oxazole dyad with tunable emission wavelengths. The application of these fluorophores as potential biomarkers has been investigated.}, doi = {10.1002/anie.201609335}, author = {Shaikh, Aslam C. and Ranade, Dnyanesh S. and Rajamohanan, Pattuparambil R. and Kulkarni, Prasad P. and Patil, Nitin T.} } @article {43361, title = {Synthesis of annulated bis-indoles through Au(I)/br{\o}nsted acid-catalyzed reactions of (1H-indol-3-yl)(aryl)methanols with 2-(arylethynyl)-1H-indoles}, journal = {Organic \& Biomolecular Chemistry}, volume = {15}, year = {2017}, month = {DEC}, pages = {863 - 869}, abstract = {A general method to access annulated bis-indoles from (1H-indol-3-yl)(aryl)methanols and 2-(arylethynyl)-1H-indoles under the catalysis of the Ph3PAuOTf/Br{\o}nsted acid binary catalyst system has been developed. The reaction was found to proceed in a highly efficient manner and benefit from easy-to-make starting materials, broad substrate scope and operational simplicity. The potential of this method has also been exemplified for the synthesis of pyrrole-annulated indoles using 2-(phenylethynyl)-1H-indoles and phenyl(1H-pyrrol-2-yl)methanols. Furthermore, the use of a ternary catalyst system, involving PdCl2/Br{\o}nsted acid/Ph3PAuOTf catalysts, has been realized for the synthesis of annulated bis-indoles starting directly from 2-(phenylbuta-1,3-diyn-1-yl)aniline and (1H-indol-3-yl)(aryl)methanol. Mechanistically, this reaction is very interesting since the overall process involves three different catalytic cycles catalyzed by three different catalysts in a relay fashion.}, doi = {10.1039/C6OB02595A}, author = {Patil, Nitin T. and Inamdar, Suleman M. and Gonnade, Rajesh Ghanshyam} } @article {44374, title = {Catalytic enantioselective 1,3-alkyl shift in alkyl aryl ethers: efficient synthesis of optically active 3,3 {\textquoteright}-diaryloxindoles}, journal = {Angewandte Chemie-International Edition}, volume = {57}, year = {2018}, month = {MAY}, pages = {5735-5739}, abstract = {Reported is the first organocatalytic asymmetric 1,3-alkyl shift in alkyl aryl ethers for the synthesis of chiral 3,3{\textquoteright}-diaryloxindoles using a chiral Bronsted acid catalyst. Preliminary results showed that each enantiomer of the 3,3{\textquoteright}-diaryloxindole, and a racemic mixture, showed different antiproliferative activities against HeLa cell lines by using an MTT assay.}, doi = {10.1002/anie.201801650}, author = {Gade, Amol B. and Bagle, Pradip N. and Shinde, Popat S. and Bhardwaj, Vipin and Banerjee, Subhrashis and Chande, Ajit and Patil, Nitin T.} } @article {44487, title = {Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes}, journal = {Organic \& Biomolecular Chemistry}, volume = {16}, year = {2018}, month = {APR}, pages = {2865-2869}, type = {Article}, abstract = {

Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.

}, doi = {10.1039/C8OB00630J}, author = {Akram, Manjur O. and Shinde, Popat S. and Chintawar, Chetan C. and Patil, Nitin T.} } @article {45399, title = { A new class of N-doped ionic PAHs via intramolecular [4+2]-cycloaddition between arylpyridines and alkynes}, journal = {Chemical Communications}, volume = {54}, year = {2018}, month = {OCT}, pages = {11909-11912}, type = {Article}, abstract = {Reported herein, for the first time, is a copper-promoted intramolecular [4+2]-cycloaddition cascade to access ionic N-doped polycyclic aromatic hydrocarbons (PAHs) with tunable emission wavelengths. It is shown that the reaction can be made catalytic with respect to Cu(OTf)(2) when an external oxidant, Selectfluor, was used.}, issn = { 1359-7345}, doi = {10.1039/c8cc05743e}, author = {Mule, Ravindra D. and Shaikh, Aslam C. and Gade, Amol B. and Patil, Nitin T.} } @article {45424, title = { Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions}, journal = {Chemical Communications}, volume = {54}, year = {2018}, month = {OCT}, pages = {11069-11083}, type = {Article}, abstract = {

The construction of C-C and C-X (X = hetero atom) bonds is the core aspect for the assembly of molecules. In this regard, late transition-metal-catalyzed cross-coupling reactions have retained their dominance for decades. Lately, gold catalysts have been emerging as a reliable contender for such transformations owing to the recent findings that reveal gold{\textquoteright}s potential beyond carbophilic -Lewis acid. The newfound ability of gold to undergo redox transformations under certain circumstances has allowed us to explore gold catalysts as a viable alternative to other late transition-metals for efficient construction of cross-coupled products. This feature article critically presents an overview of all the redox neutral cross-coupling reactions enabled by gold catalysis, which we believe would stimulate further research activities in this promising area.

}, isbn = {1359-7345}, doi = {10.1039/c8cc05601c}, author = {Akram, Manjur O. and Banerjee, Somsuvra and Saswade, Sagar S. and Bedi, Vaibhav and Patil, Nitin T.} } @article {44623, title = {Visible light mediated desilylative C(sp(2))-C(sp(2)) cross-coupling reactions of arylsilanes with aryldiazonium salts under Au(i)/Au(iii) catalysis}, journal = {Chemical Communications}, volume = {54}, year = {2018}, month = {JUL}, pages = {7223-7226}, abstract = {

Desilylative C(sp(2))-C(sp(2)) cross-coupling reactions of arylsilanes with aryldiazonium salts under Au(i)/photoredox catalysis have been reported. The addition of Cu-salts as catalysts was found to be crucial for the success of this transformation.

}, issn = {1359-7345}, doi = {10.1039/c8cc03925a}, author = {Chakrabarty, Indradweep and Akram, Manjur O. and Biswas, Suprakash and Patil, Nitin T.} } @article {46142, title = {External oxidant-dependent reactivity switch in copper-mediated intramolecular carboamination of alkynes: access to a different class of fluorescent ionic nitrogen-doped polycyclic aromatic hydrocarbons}, journal = {Journal of Organic Chemistry}, volume = {84}, year = {2019}, month = {APR }, pages = {4120-4130}, type = {Article}, abstract = {

An interesting case of external oxidant-controlled reactivity switch leading to a divergent set of ionic nitrogen-doped polycyclic aromatic hydrocarbons (N-doped PAHs), is presented here, which is quite unrecognized in copper-mediated reactions. In the current scenario, from the same pyridino-alkyne substrates, the use of the external oxidant Ph1(0Ac)2, in combination with Cu(OTf)(2), gave N-doped spiro-PAHs via a dearomative 1,2-carboamination process; whereas, without the use of oxidant, an alkyne/azadiene [4 + 2]-cycloaddition cascade occurred to exclusively afford ionic N-doped PAHs. These newly synthesized N-doped PAHs further exhibit tunable emissions, as well as excellent quantum efficiencies.

}, issn = {0022-3263}, doi = {10.1021/acs.joc.9b00120}, author = {Shaikh, Aslam C. and Banerjee, Somsuvra and Mule, Ravindra D. and Bera, Saibal and Patil, Nitin T.} } @article {45518, title = {Gold-catalyzed 1,2-oxyalkynylation of N-Allenamides with ethylnylbenziodoxolones}, journal = {Organic Letters}, volume = {21}, year = {2019}, month = {JAN}, pages = {180-184}, type = {Article}, abstract = {

A gold-catalyzed 1,2-oxyalkynylation of N-allenamides with ethylnylbenziodoxolones (EBXs) has been achieved for the first time. The reaction, which follows a redox-neutral Au(I)/Au(III) catalytic pathway, was enabled in an attempt to exhaust the EBX reagents atom-economically by putting the nucleophilic carboxylate part of EBXs to appropriate use. This constitutes the first example for gold-catalyzed beta-alkynylation of N-allenamides to construct highly valuable 1,3-enynes. The potential of the sequence is further documented by some follow-up transformations.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.8b03651}, author = {Banerjee, Somsuvra and Senthilkumar, Beeran and Patil, Nitin T.} } @article {46282, title = {Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-Diynes: An expedient access to luminescent cycl[3.2.2]azines}, journal = {Organic Letters}, volume = {21}, year = {2019}, month = {SEP}, pages = {7109-7113}, type = {Article}, abstract = {

Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.

}, doi = {10.1021/acs.orglett.9b02677}, author = {Chintawar, Chetan C. and Mane, Manoj V. and Tathe, Akash G. and Biswas, Suprakash and Patil, Nitin T.} } @article {45519, title = {Gold(I)-catalyzed hydroxy group assisted C(sp(2))-H alkylation of enaminones with diazo compounds to access 3-alkyl chromones}, journal = {Organic Letters}, volume = {21}, year = {2019}, month = {JAN }, pages = {335-339}, type = {Article}, abstract = {

A strategy for expedient synthesis of 3-substituted chromones from easily available o-hydroxyarylenaminones and diazo compounds has been developed. Carefully conducted experimental and computational studies led us to propose an uncommon mechanistic pathway involving the hydroxyl group assisted alkylation of enaminones with in situ generated gold carbenes.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.8b03989}, author = {Bagle, Pradip N. and Mane, Manoj V. and Sancheti, Shashank P. and Gade, Amol B. and Shaikh, Samir R. and Baik, Mu-Hyun and Patil, Nitin T.} } @article {46192, title = {Ionic pyridinium-oxazole dyads: design, synthesis, and application in mitochondrial imaging}, journal = {Journal of Organic Chemistry}, volume = {84}, year = {2019}, month = {FEB }, pages = {1766-1777}, type = {Article}, abstract = {

We recently developed an oxidative intramolecular 1,2-amino-oxygenation reaction, combining gold(I)/gold(III) catalysis, for accessing structurally unique ionic pyridinium-oxazole dyads (PODs) with tunable emission wavelengths. On further investigation, these fluorophores turned out to be potential biomarkers; in particular, the one containing -NMe2 functionality (NMe2-POD) was highly selective for mitochondrial imaging. Of note, because of mitochondria{\textquoteright}s involvement in early-stage apoptosis and degenerative conditions, tracking the dynamics of mitochondrial morphology with such imaging technology has attracted much interest. Along this line, we wanted to build a library of such PODs which are potential mitochondria trackers. However, Au/Selecfluor, our first-generation catalyst system, suffers from undesired fluorination of electronically rich PODs resulting in an inseparable mixture (1:1) of the PODs and their fluorinated derivatives. In our attempt to search for a better alternative to circumvent this issue, we developed a second-generation approach for the synthesis of PODs by employing Cu(II)/PhI(OAC)(2)-mediated oxidative 1,2-amino-oxygenation of alkynes. Thes newly synthesized PODs exhibit tunable emissions as well as excellent quantum efficiency up to 0.96. Further, this powerful process gives rapid access to a library of NMe2-PODs which are potential mitochondrial imaging agents. Out of the library, the randomly chosen POD-3g was studied for cell-imaging experiments which showed high mitochondrial specificity, superior photostability, and appreciable tolerance to microenvironment changes with respect to commercially available MitoTracker green.

}, issn = {0022-3263}, doi = {10.1021/acs.joc.8b02528}, author = {Shaikh, Aslam C. and Varma, Mokshada E. and Mule, Ravindra D. and Banerjee, Somsuvra and Kulkarni, Prasad P. and Patil, Nitin T.} } @article {46338, title = {Ligand-enabled gold-catalyzed C(sp(2))-n cross-coupling reactions of aryl iodides with amines}, journal = {Organic Letters}, volume = {21}, year = {2019}, month = {OCT }, pages = {8101-8105}, type = {Article}, abstract = {

The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.9b03082}, author = {Akram, Manjur O. and Das, Avishek and Chakrabarty, Indradweep and Patil, Nitin T.} } @article {46317, title = {Ortho-oxygenative 1,2-difunctionalization of diarylalkynes under merged gold/organophotoredox relay catalysis}, journal = {Chemistry-An Asian Journal}, year = {2019}, month = {OCT}, type = {Article; Early Access}, abstract = {

Reported herein is an ortho-oxygenative 1,2-difunctionalization of diarylalkynes under merged gold/organophotoredox catalysis to access highly functionalized 2-(2-hydroxyaryl)-2-alkoxy-1-arylethan-1-ones. Detailed mechanistic studies suggested a relay process, initiating with gold-catalyzed hydroalkoxylation of alkynes, to generate enol-ether followed by a key formal [4+2]-cycloaddition reaction. The successful application of the present methodology was also shown for the synthesis of benzofurans.

}, keywords = {binary catalyst system, Gold catalysis, organocatalyst, photoredox, synthetic methodology}, issn = {1861-4728}, doi = {10.1002/asia.201901275}, author = {Sancheti, Shashank P. and Akram, Manjur O. and Roy, Rupam and Bedi, Vaibhav and Kundu, Shubhankar and Patil, Nitin T.} } @article {46934, title = {Gold and hypervalent iodine(iii): liaisons over a decade for electrophilic functional group transfer reactions}, journal = {Chemical Communications}, volume = {56}, year = {2020}, month = {MAR }, pages = {2677-2690}, type = {Article}, abstract = {

Over the last two decades, hypervalent iodine(iii) reagents have evolved from being {\textquoteleft}bonding curiosities{\textquoteright} to mainstream reagents in organic synthesis, in particular, electrophilic functional group transfer reactions. In this context, gold catalysts have not only emerged as a unique toolbox to facilitate such reactions (especially alkynylations) but also opened new possibilities with their different modes of reactivities for other functional group transfer reactions (acetoxylations and arylations). This feature article critically summarizes hitherto all such Au-catalyzed electrophilic functional group transfer reactions with hypervalent iodine(iii) reagents, emphasizing their mechanistic aspects.

}, issn = {1359-7345}, doi = {10.1039/d0cc00106f}, author = {Banerjee, Somsuvra and Bhoyare, Vivek W. and Patil, Nitin T.} } @article {46819, title = {Gold-catalyzed alkynylative meyer-schuster rearrangement}, journal = {Organic Letters}, volume = {22}, year = {2020}, month = {JUN}, pages = {4792-4796}, type = {Article}, abstract = {

By applying the {\textquoteleft}{\textquoteleft}interplay{\textquoteright}{\textquoteright} mode, which consolidates two key reactivity modes of gold catalysis, namely pi-activation mode and cross-coupling mode, the first alkynylative Meyer-Schuster rearrangement is designed and successfully implemented. The current protocol gives straightforward access to enynones, a highly valuable building block, from easily available propargyl alcohol feedstocks. Control experiments suggest an Au(III) catalyst triggers the Meyer-Schuster rearrangement, whereas monitoring the reaction with ESI-HRMS provided strong evidence in favor of a key alkynylgold(III) intermediate which supports the proposed {\textquoteleft}{\textquoteleft}interplay{\textquoteright}{\textquoteright} scenario.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.0c01596}, author = {Banerjee, Somsuvra and Ambegave, Shivhar B. and Mule, Ravindra D. and Senthilkumar, Beeran and Patil, Nitin T.} } @article {48205, title = {BQ-AurIPr: a redox-active anticancer Au(i) complex that induces immunogenic cell death}, journal = {Chemical Science}, volume = {13}, year = {2022}, month = {SEP}, pages = {10779-10785}, type = {Article}, abstract = {

Immunogenic Cell Death (ICD) is a unique cell death mechanism that kills cancer cells while rejuvenating the anticancer immunosurveillance, thereby benefiting the clinical outcomes of various immuno-chemotherapeutic regimens. Herein, we report development of a library of benzo[a]quinolizinium-based Au(i) complexes through an intramolecular amino-auration reaction of pyridino-alkynes. We tested 40 candidates and successfully identified BQ-AurIPr as a novel redox-active Au(i) complex with potent anticancer properties. BQ-AurIPr efficiently triggered generation of DAMPs - the hallmarks of ICD - and was superior in terms of efficiency compared to FDA-approved drugs known to induce ICD. BQ-AurIPr significantly increased immunogenicity of cancer cells enhancing their phagocytosis when co-cultured with immune cells. Our investigation reveals that BQ-AurIPr induces oxidative stress inside mitochondria leading to mitophagy, as the mechanism for immunogenic cell death in A549 cells.

}, issn = {2041-6520}, doi = {10.1039/d2sc03756d}, author = {Mule, Ravindra D. and Kumar, Akhilesh and Sancheti, Shashank P. and Senthilkumar, B. and Kumar, Himanshu and Patil, Nitin T.} } @article {48191, title = {Enantioselective Au(I)/Au(III) redox catalysis enabled by chiral (P,N)-ligands}, journal = {Journal of the American Chemical Society}, volume = {144}, year = {2022}, month = {APR}, pages = {7089-7095}, type = {Article}, abstract = {

Presented herein is the first report of enantioselective Au(I)/Au(III) redox catalysis, enabled by a newly designed hemilabile chiral (P,N)-ligand (ChetPhos). The potential of this concept has been demonstrated by the development of enantioselective 1,2-oxyarylation and 1,2-aminoarylation of alkenes which provided direct access to the medicinally relevant 3-oxy- and 3-aminochromans (up to 88\% yield and 99\% ee). DFT studies were carried out to unravel the enantiodetermining step, which revealed that the stronger trans influence of phosphorus allows selective positioning of the substrate in the C-2-symmetric chiral environment present around nitrogen, imparting a high level of enantioselectivity.

}, issn = {0002-7863}, doi = {10.1021/jacs.2c02799}, author = {Chintawar, Chetan C. and Bhoyare, Vivek W. and Mane, Manoj V. and Patil, Nitin T.} } @article {48128, title = {Interplay of anion-pi(+) and pi(+)-pi(+) interactions in novel pyrido[2,1-a]isoquinolinium-based aiegens - substituent- and counterion-dependent fluorescence modulation and applications in live cell mitochondrial imaging}, journal = {Chemistry-A European Journal}, volume = {28}, year = {2022}, month = {JUL }, pages = {e202200632}, type = {Article}, abstract = {

Recently, the concept of anion-pi(+) interactions has witnessed unique applications in the field of AIEgen development. In this contribution, we disclose a consolidated study of a library of N-doped ionic AIEgens accessed through silver-mediated cyclization of pyridino-alkynes. A thorough photophysical, computational and crystallographic study has been conducted to rationalize the observed substituent- and counterion-dependent fluorescence properties of these luminogens. We further elucidate the prominent role of anion-pi(+) interactions, pi(+)-pi(+) interactions and other non-covalent interactions, in inhibiting the undesired ACQ effect. Finally, we have also demonstrated the application of selected AIEgens for imaging of mitochondria in live cells.

}, keywords = {1-a]isoquinolinium, AIEgens, anion-pi(+), crystal structure, mitochondrial imaging, pyrido[2}, issn = {0947-6539}, doi = {10.1002/chem.202200632}, author = {Mule, Ravindra D. and Roy, Rupam and Mandal, Koushik and Chopra, Deepak and Dutta, Tanoy and Sancheti, Shashank P. and Shinde, Popat S. and Banerjee, Somsuvra and Lal Koner, Apurba and Bhowal, Rohit and Senthilkumar, Beeran and Patil, Nitin T.} }