Issue 74, 2021

Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis

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.

Graphical abstract: Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis

Supplementary files

Article information

Article type
Communication
Submitted
08 Jul 2021
Accepted
12 Aug 2021
First published
12 Aug 2021

Chem. Commun., 2021,57, 9414-9417

Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis

X. Zhao, S. Zhu, F. Qing and L. Chu, Chem. Commun., 2021, 57, 9414 DOI: 10.1039/D1CC03668H

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