A new CC bond formation strategy based on enantioselective radical alkylation of C(sp3)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 CH 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.
Chemical Science – Royal Society of Chemistry
Published: May 18, 2018
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