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Photo-induced copper-catalyzed alkynylation and amination of remote unactivated C(sp3)-H bonds
Authors:Zhusong Cao  Jianye Li  Youwen Sun  Hanwen Zhang  Xueling Mo  Xin Cao  Guozhu Zhang
Institution:Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 P. R. China.; College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan Hubei 430079 P. R. China ; Zhongshan Hospital, Fudan University, 180 Fenglin Road, Shanghai 200032 P. R. China,
Abstract:A method for remote radical C–H alkynylation and amination of diverse aliphatic alcohols has been developed. The reaction features a copper nucleophile complex formed in situ as a photocatalyst, which reduces the silicon-tethered aliphatic iodide to an alkyl radical to initiate 1,n-hydrogen atom transfer. Unactivated secondary and tertiary C–H bonds at β, γ, and δ positions can be functionalized in a predictable manner.

Remote C−H alkynylation and amination of aliphatic alcohols.
Keywords:
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