Nickel-Catalyzed Acylation of Aryl Bromides with Acyl Imidazoles

12 July 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Alkyl imidazolides were herein found to be viable coupling partners for the Ni-catalyzed acylation of aryl bromides. This cross-coupling reaction features a broad substrate scope and be performed in an extremely cost-efficient fashion. Mechanistically, formation of acyl radicals via reduction of imidazolides represents a major departure from other reported radical acylation reactions. Of particular note, extensive studies revealed an intriguing radical chain mechanism and a remarkable CO-extrusion-recombination phenomenon. Finally, the practicality of this cross-coupling was demonstrated with a gram-scale reaction for the synthesis of a furan diterpenoid natural product.


Radical Cross-Coupling Reaction
Reductive Cross-Coupling
carbonylation pathway

Supplementary materials



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