Visible Light Driven Alkylation of C(sp3)-H Bonds Enabled by 1,6-Hydrogen Atom Transfer/Radical Relay Addition

Zhi-Yong Ma; Li-Na Guo; Ying You; Fan Yang; Mingyou Hu; Xin-Hua Duan

doi:10.1021/acs.orglett.9b01804

Visible Light Driven Alkylation of C(sp³)-H Bonds Enabled by 1,6-Hydrogen Atom Transfer/Radical Relay Addition

Org Lett. 2019 Jul 19;21(14):5500-5504. doi: 10.1021/acs.orglett.9b01804. Epub 2019 Jun 27.

Authors

Zhi-Yong Ma¹, Li-Na Guo¹, Ying You¹, Fan Yang¹, Mingyou Hu¹, Xin-Hua Duan^{1

2}

Affiliations

¹ Department of Chemistry, School of Science, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter , Xi'an Jiaotong University , Xi'an 710049 , P. R. China.
² State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou 730000 , P. R. China.

PMID: 31246029
DOI: 10.1021/acs.orglett.9b01804

Abstract

A visible-light-driven sulfamate esters guided alkylation of unactivated C(sp³)-H bonds enabled by a 1,6-HAT/radical addition cascade is described. Not only structurally diverse Michael acceptors but also styrenes are amenable to this alkylation reaction. Notably, the N-H bonds activation radical relay refrained from prefunctionalization and using excess external oxidants.