Photo-induced copper-catalyzed alkynylation and amination of remote unactivated C(sp3)-H bonds

Zhusong Cao; Jianye Li; Youwen Sun; Hanwen Zhang; Xueling Mo; Xin Cao; Guozhu Zhang

doi:10.1039/D0SC05883A

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Photo-induced copper-catalyzed alkynylation and amination of remote unactivated C(sp³)-H bonds†

Zhusong Cao,^a Jianye Li,^b Youwen Sun,^a Hanwen Zhang,^a Xueling Mo,^a Xin Cao

*^c and Guozhu Zhang

*^ab

Author affiliations

* Corresponding authors

^a 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
E-mail: guozhuzhang@sioc.ac.cn

^b College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China

^c Zhongshan Hospital, Fudan University, 180 Fenglin Road, Shanghai 200032, P. R. China
E-mail: caox@fudan.edu.cn

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.

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Article information

DOI: https://doi.org/10.1039/D0SC05883A
Article type: Edge Article
Submitted: 26 Oct 2020
Accepted: 14 Feb 2021
First published: 16 Feb 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2021,12, 4836-4840

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Photo-induced copper-catalyzed alkynylation and amination of remote unactivated C(sp³)-H bonds

Z. Cao, J. Li, Y. Sun, H. Zhang, X. Mo, X. Cao and G. Zhang, Chem. Sci., 2021, 12, 4836 DOI: 10.1039/D0SC05883A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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