@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 {47638,
	title = {Ni(II)-catalyzed intramolecular C-H/C-H oxidative coupling: an efficient route to functionalized cycloindolones and indenoindolones},
	journal = {ACS Catalysis},
	volume = {11},
	year = {2021},
	month = {OCT },
	pages = {12384-12393},
	type = {Article},
	abstract = {Nickel(II)-catalyzed intramolecular C(sp(2))-H/C(sp(3))-H and C(sp(2))-H/C(sp(2))-H oxidative couplings in indoles are achieved via chelation assistance. These reactions provide access to biologically relevant five- and six-membered substituted cyclopentaindolones, carbazolones, and indenoindolones in high yields and good chemoselectivity employing an air-stable and defined nickel catalyst, (bpy)Ni(OAc)(2). The oxidative cyclizations proceeded either through a six-membered or an unconventional seven-membered nickelacycle. An extensive mechanistic investigation by experiments and theoretical calculations revealed a facile indole{\textquoteright}s C(2)-H nickelation and a rate-limiting reductive elimination process. This intramolecular oxidative cyclization operates via a probable Ni(II)/Ni(III) pathway involving single-electron oxidation of nickel without the participation of a carbon-based radical.},
	keywords = {C-H activation, cycloindolones, indenoindolones, indoles, Mechanism, Nickel, oxidative coupling},
	issn = {2155-5435},
	doi = {10.1021/acscatal.1c03314},
	author = {Ankade, Shidheshwar B. and Samal, Pragnya Paramita and Soni, Vineeta and Gonnade, Rajesh G. and Krishnamurty, Sailaja and Punji, Benudhar}
}
