Affiliation:
1. Department of Chemistry Zhejiang University Hangzhou 310027 Zhejiang Province P. R. China
2. Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province Department of Chemistry School of Science and Research Center for Industries of the Future Westlake University Hangzhou 310030 Zhejiang Province P. R. China
3. Institute of Natural Sciences Westlake Institute for Advanced Study Hangzhou 310024 Zhejiang Province P. R. China
Abstract
AbstractFunctionalization of C(sp3)−H bonds adjacent to a nitrogen atom is an efficient means of preparing structurally complex amines and has long been of interest to synthetic chemists. Herein, dual palladium catalysis is used to achieve α‐C−H arylation of linear N‐sulfonyl amines with aryl boroxines, rather than N‐arylation (C−N bond formation). This method has a broad scope with respect to both the amine and the boroxine, providing convenient access to α‐branched amines. During the dehydrogenation step of the catalytic cycle, bromobenzene accepts a hydride from the α‐carbon on the amine, producing an imine that subsequently undergoes Pd‐catalyzed C‐arylation with the boroxine. Mechanistic studies revealed that imine arylation proceeds through an unusual Pd0/PdII catalytic cycle, in which oxidative cyclization of a palladium η2‐imine complex generates a three‐membered palladacycle that subsequently undergoes transmetallation reaction with the boroxine.
Subject
Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis
Cited by
1 articles.
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