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A new C-C bond formation strategy based on enantioselective radical alkylation of C(sp 3 )-H bonds via Co(ii)-based metalloradical catalysis has been demonstrated for stereoselective synthesis of chiral indolines. The Co(ii)-based system enables activation of aryldiazomethanes as radical precursors at room temperature for enantioselective intramolecular radical alkylation of broad types of C-H bonds, constructing 2-substituted indolines in high yields with excellent enantioselectivities. In addition to chemoselectivity and regioselectivity, this Co(ii)-catalyzed alkylation features tolerance to functional groups and compatibility with heteroaryl substrates. Detailed mechanistic studies provide insight into the underlying stepwise radical pathway.

Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp3)–H bonds

Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp³)–H bonds