Issue 22, 2018

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

Abstract

A new C–C 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 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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Mar 2018
Accepted
12 May 2018
First published
14 May 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 5082-5086

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

X. Wen, Y. Wang and X. P. Zhang, Chem. Sci., 2018, 9, 5082 DOI: 10.1039/C8SC01476K

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