Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis

Xian Zhao; Shengqing Zhu; Feng-Ling Qing; Lingling Chu

doi:10.1039/d1cc03668h

Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis

Chem Commun (Camb). 2021 Sep 16;57(74):9414-9417. doi: 10.1039/d1cc03668h.

Authors

Xian Zhao¹, Shengqing Zhu¹, Feng-Ling Qing^{1

2}, Lingling Chu¹

Affiliations

¹ State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai 201620, China. Lingling.chu1@dhu.edu.cn.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China.

PMID: 34528966
DOI: 10.1039/d1cc03668h

Abstract

A photoredox/nickel dual catalyzed reductive hydrobenzylation of alkynes and benzyl chlorides by employing alkyl amines as a stoichiometric reductant is described. This synergistic protocol proceeds via Markovnikov-selective migratory insertion of an alkyne into nickel hydride, followed by cross-coupling with benzyl chloride, providing facile access to important 1,1-disubstituted olefins. This reaction enables the generation of nickel hydride by utilizing readily available alkyl amines as the hydrogen source. The mild conditions are compatible with a wide range of aryl and alkyl alkynes as well as chlorides.