Issue 14, 2024

Photoelectrochemical nickel-catalyzed carboacylation/silanoylation of alkenes with unactivated C/Si–H bonds

Abstract

Direct and selective installation of two different functional groups into the unsaturated bonds of alkenes constitutes a long-standing goal in organic synthesis. Herein, we first report a photoelectrochemical approach for the carboacylation/silanoylation of alkenes with unactivated alkanes/hydrosilanes via the LMCT process. A number of ketones with high complexity and diversity were rapidly obtained from commercially available materials in an economical and sustainable manner. Furthermore, this protocol can be scaled up to the gram-level. This paired electrocatalysis strategy features excellent regioselectivity, and ample substrate scope, is external-oxidant-free, and features a high resource economy. A series of mechanistic experiments were performed to determine the preferred pathway for the photoelectrochemical Ni(I)/Ni(II)/Ni(III) cycles in these transformations.

Graphical abstract: Photoelectrochemical nickel-catalyzed carboacylation/silanoylation of alkenes with unactivated C/Si–H bonds

Supplementary files

Article information

Article type
Paper
Submitted
25 Oct 2023
Accepted
12 Feb 2024
First published
13 Feb 2024

Green Chem., 2024,26, 8315-8322

Photoelectrochemical nickel-catalyzed carboacylation/silanoylation of alkenes with unactivated C/Si–H bonds

L. Wang, X. Huo, X. He, L. Ackermann and D. Wang, Green Chem., 2024, 26, 8315 DOI: 10.1039/D3GC04109C

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