@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 {48957,
	title = {Iron-catalyzed regioselective C-H alkylation of indoles: an additive-free approach in renewable solvent},
	journal = {Green Chemistry },
	volume = {25},
	year = {2023},
	month = {NOV },
	pages = {9733-9743},
	type = {Journal Article},
	abstract = {<p>Alkylated indoles are important motifs in various biologically active molecules and drug candidates. Herein, we report a mild and efficient iron-catalyzed protocol for synthesizing alkylated indoles via C-H bond alkylation of indoles with unactivated alkenes, demonstrating a high level of regioselectivity. The reaction occurs under additive-free, solvent-free (or trace green solvent, 2-MeTHF) and less energy-intensive conditions using a sustainable metal catalyst and provides easy access to privileged alkylated indoles with anti-Markovnikov selectivity. Alkylation is compatible with important functionalities, such as fluoro, chloro, trifluoromethyl, alkenyl, ether, thioether, silyl, and siloxane, including heteroaryl, pyridinyl, carbazolyl, and indolyl moieties (45 examples, up to 96\% yield). The developed protocol is very simple, straightforward, and fully accords with the principles of green chemistry. A detailed mechanistic investigation manifests the facile indole{\textquoteright}s C-H activation at the Fe(0) center, reversible 1,2-insertion of the alkene into the Fe-H bond of a metallacycle, and a turnover-limiting reductive elimination. Alkylated indoles are important motifs in various biologically active molecules and drug candidates.</p>
},
	keywords = {Aromatic Ketones, Green, organic synthesis},
	issn = {1463-9262},
	doi = {10.1039/d3gc03709f},
	author = {Pradhan, Chandini and Jagtap, Rahul A. and Samal, Pragnya Paramita and Krishnamurty, Sailaja and Punji, Benudhar}
}
