Nickel-Catalyzed Cross-Electrophile Coupling of 1,2,3-Benzotriazin-4(3<i>H</i>)-ones with Aryl Bromides
Tingzhi Lin, Yan‐En Wang, Ning Cui, Miaohui Li, Rui Wang, Jiahui Bai, YiRan Fan, Dan Xiong, Fei Xue, Patrick J. Walsh, Jianyou Mao
Abstract
The nickel-catalyzed cross-electrophile coupling of 1,2,3-benzotriazin-4(3H)-ones with aryl bromides to generate a diverse array of ortho-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.
Topics & Concepts
ElectrophileBenzamideArylChemistryNickelCatalysisYield (engineering)Medicinal chemistryRing (chemistry)Combinatorial chemistryOrganic chemistryMaterials scienceMetallurgyAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsPhenothiazines and Benzothiazines Synthesis and Activities