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Visible-Light-Promoted Remote C(sp3)–H Amidation and Chlorination

Author:
Qin, Qixue, Yu, Shouyun
Source:
Organic letters 2015 v.17 no.8 pp. 1894-1897
ISSN:
1523-7052
Subject:
ambient temperature, chemical structure, chlorides, chlorination, organic compounds, photocatalysts, regioselectivity
Abstract:
A visible-light-promoted C(sp³)–H amidation and chlorination of N-chlorosulfonamides (NCSs) is reported. This remote C(sp³)–H functionalization can be achieved in weak basic solution at room temperature with as little as 0.1 mol % of a photocatalyst. A variety of nitrogen-containing heterocycles (up to 94% yield) and chlorides (up to 93% yield) are prepared from NCSs. Late-stage C(sp³)–H functionalization of complex and biologically important (−)-cis-myrtanylamine and (+)-dehydroabietylamine derivatives can also be achieved with excellent yields and regioselectivity.
Agid:
5790464