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Nickel-Catalyzed Acylation of Aryl Bromides with Acyl Imidazoles

preprint
submitted on 12.07.2019 and posted on 12.07.2019 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.

History

Email Address of Submitting Author

lichao@nibs.ac.cn

Institution

National Institute of Biological Sciences, Beijing

Country

China

ORCID For Submitting Author

0000-0003-4529-5570

Declaration of Conflict of Interest

no conflict of interest

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