Site-Tunable Csp3-H Bonds Functionalization by Visible-Light-Induced Radical Translocation of N-Alkoxyphthalimides

Chuanyong Wang; Yangyang Yu; Wen-Long Liu; Wei-Liang Duan

doi:10.1021/acs.orglett.9b03524

Site-Tunable C_sp³-H Bonds Functionalization by Visible-Light-Induced Radical Translocation of N-Alkoxyphthalimides

Org Lett. 2019 Nov 15;21(22):9147-9152. doi: 10.1021/acs.orglett.9b03524. Epub 2019 Oct 31.

Authors

Chuanyong Wang¹, Yangyang Yu¹, Wen-Long Liu¹, Wei-Liang Duan¹

Affiliation

¹ College of Chemistry and Chemical Engineering , Yangzhou University , 180 Siwangting Road , Yangzhou 225002 , China.

PMID: 31670519
DOI: 10.1021/acs.orglett.9b03524

Abstract

Site-tunable functionalization of C(sp³)-H bonds has been accomplished through radical translocation and cross-coupling. Upon irradiation with visible light, copper-based photocatalyst [Cu(Xantphos)(dmp)]BF₄ enabled cross-coupling of N-alkoxyphthalimides with amino acid esters or amino acids to provide δ-C(sp³)-H alkylated alcohols (31 examples, up to 92% yield) with additive BNDHP or α-C(sp³)-H alkylated alcohols (18 examples, up to 86% yield) with additive DABCO in a highly regioselective fashion.

Publication types

Research Support, Non-U.S. Gov't