Issue 81, 2023

Swift C–C bond insertion by a 12-electron palladium(0) surrogate

Abstract

The selective activation of C–C bonds holds vast promise for catalysis. So far, research has been primarily directed at rhodium and nickel under harsh reaction conditions. Herein, we report C–C insertion reactions of a 12-electron palladium(0) surrogate stabilized by a cyclic(alkyl)(amino) carbene (CAAC) ligand. Benzonitrile (1), biphenylene (2), benzocyclobutenone (3), and naphtho[b]cyclopropene (4) were studied. These substrates allow elucidation of the effect of ring strain as well as hybridization encompassing sp3, sp2 and sp hybridized carbon atoms. All reactions proceed quantitatively at or below room temperature. This work therefore outlines perspectives for mild C–C bond functionalization catalysis.

Graphical abstract: Swift C–C bond insertion by a 12-electron palladium(0) surrogate

Supplementary files

Article information

Article type
Communication
Submitted
16 8 2023
Accepted
14 9 2023
First published
14 9 2023
This article is Open Access
Creative Commons BY license

Chem. Commun., 2023,59, 12104-12107

Swift C–C bond insertion by a 12-electron palladium(0) surrogate

K. Breitwieser, F. Dankert, A. Grünwald, P. R. Mayer, F. W. Heinemann and D. Munz, Chem. Commun., 2023, 59, 12104 DOI: 10.1039/D3CC03964A

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