@article {46798,
	title = {Iron-catalyzed C(sp(2))-H alkylation of indolines and benzo[h]quinoline with unactivated alkyl chlorides through chelation assistance},
	journal = {ACS Catalysis},
	volume = {10},
	year = {2020},
	month = {JUL },
	pages = {7312-7321},
	type = {Article},
	abstract = {<p>Regioselective C-H bond alkylation of indolines and benzo[h]quinoline with a wide range of unactivated and highly demanded primary and secondary alkyl chlorides is accomplished using a low-cost iron catalyst. This reaction tolerates diverse functionalities, such as C(sp(2))-Cl, fluoro, alkenyl, silyl, ether, thioether, pyrrolyl, and carbazolyl groups including cyclic and acyclic alkyls as well as alkyl-bearing fatty-alcohol and polycyclic-steroid moieties. The demonstrated iron-catalyzed protocol proceeded via either a five-membered or a six-membered metallacycle. Intriguingly, the C-7-alkylated indolines can be readily functionalized into free-NH indolines/indoles and tryptamine derivatives. A detailed mechanistic investigation highlights the participation of an active Fe(I) catalyst and the involvement of a halogen-atom transfer process via a single-electron-based mechanism. Deuterium labeling and kinetics analysis indicate that the C-H metalation of indoline is the probable turnover-limiting step. Overall, the experimental and theoretical studies supported an Fe(I)/Fe(III) pathway for the alkylation reaction comprising the two-step, one-electron oxidative addition of alkyl chloride.</p>
},
	keywords = {alkyl chlorides, Alkylation, C-H activation, chelation assistance, indolines, iron},
	issn = {2155-5435},
	doi = {10.1021/acscatal.0c02030},
	author = {Jagtap, Rahul A. and Samal, Pragnya Paramita and Vinod, C. P. and Krishnamurty, Sailaja and Punji, Benudhar}
}
@article {48083,
	title = {Efficient route to 3,3 {\textquoteleft}-biindolinylidene-diones by iron-catalyzed dimerization of isatins},
	journal = {Chemistry-an Asian Journal},
	volume = {17},
	year = {2022},
	month = {AUG},
	pages = {e202200414},
	type = {Article},
	abstract = {<p>
	Iron-catalyzed dimerization of various isatin derivatives is described for the efficient synthesis of 3,3 {\textquoteleft}-biindolinylidene-diones (isoindigos). The reaction provides easy access to self-coupled and cross-coupled 3,3 {\textquoteleft}-indolinylidene-diones that have high relevance to biology and materials. This Fe(0)- or Fe(II)-catalyzed dimerization reaction tolerates a wide range of functionalities, such as fluoro, chloro, bromo, alkenyl, nitrile, ether, ester, pyrrolyl, indolyl and carbazolyl groups, including cyclic and acyclic alkyls as well as an alkyl-bearing fatty-alcohol moiety. Especially, the coupling between two distinct isatins provided excellent selectivity for the cross-dimerization with trace of self-couplings. The single-crystal X-ray diffraction study established the molecular structure of eight dimerized products. A preliminary mechanistic study of the Fe-catalyzed dimerization supported the radical pathway for the reaction.</p>
},
	keywords = {Cross-coupling, dimerization, iron, Isatin, Isoindigo, Mechanism},
	issn = {1861-4728},
	doi = {10.1002/asia.202200414},
	author = {Jagtap, Rahul A. and Pradhan, Chandini and Gonnade, Rajesh G. and Punji, Benudhar}
}
