Issue 4, 2024

Nickel/photoredox dual-catalyzed reductive cross-coupling of aryl halides and aldehydes

Abstract

A straightforward reductive cross-coupling of aryl halides and aldehydes to afford silyl-protected secondary alcohols is reported. The catalytic system features the use of nickel/photoredox dual catalysis and α-silylamine as a mild, easily accessible organic reductant, thus enabling the coupling process to occur smoothly under mild conditions without the necessity of pre-preparing highly reactive organometallic reagents and using stoichiometric amounts of metal-based reductants (such as Mn and Zn). The key to the success of this reductive coupling is to identify α-silylamine as a bifunctional organic reductant that simultaneously serves as a reducing agent and a transmetallic reagent to restore the nickel catalyst. The reaction shows a broad substrate scope and tolerates various functional groups, and a variety of (hetero)aryl and aliphatic aldehydes are compatible, thus providing a complementary approach towards Zn/Mn-mediated reductive coupling systems.

Graphical abstract: Nickel/photoredox dual-catalyzed reductive cross-coupling of aryl halides and aldehydes

Supplementary files

Article information

Article type
Research Article
Submitted
20 Nov 2023
Accepted
28 Dec 2023
First published
02 Jan 2024

Org. Chem. Front., 2024,11, 1205-1210

Nickel/photoredox dual-catalyzed reductive cross-coupling of aryl halides and aldehydes

J. Liu, Y. Chen, H. Zhao and W. Yuan, Org. Chem. Front., 2024, 11, 1205 DOI: 10.1039/D3QO01927F

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