Nickel-Catalyzed Cross-Electrophile Coupling of 1,2,3-Benzotriazin-4(3)-ones with Aryl Bromides.

J Org Chem

Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China.

Published: December 2022

The nickel-catalyzed cross-electrophile coupling of 1,2,3-benzotriazin-4(3)-ones with aryl bromides to generate a diverse array of -arylated benzamide derivatives has been developed. The reaction displayed good functional group tolerance with Zn as the reductant. The key to this transformation is the ring opening of benzotriazinones, which undergo a denitrogenative process to obtain various benzamide derivatives (29 examples, 42-93% yield). The scalability of this transformation was demonstrated.

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http://dx.doi.org/10.1021/acs.joc.2c02246DOI Listing

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