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Nickel-Catalyzed Acylation of Aryl Bromides with Acyl Imidazoles
preprintsubmitted on 12.07.2019, 11:49 and posted on 12.07.2019, 17:43 by Junming Zhuo, Yong Zhang, Zijian Li, Chao Li
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.