Affiliation:
1. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research Ministry of Education of China Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province College of Chemistry and Chemical Engineering Hunan Normal University Changsha Hunan 410081 China
2. State Key Laboratory of Structure Chemistry Center for Excellence in Molecular Synthesis Fujian Institute of Research on the Structure of Matter Fujian College Chinese Academy of Sciences Fuzhou Fujian 350002 China
3. School of Chemical Sciences University of the Chinese Academy of Sciences Beijing 100049 China
Abstract
Abstract“Through space” palladium/hydrogen shift is an efficient strategy to achieve selective functionalization of a specific remote C−H bond. Compared with relatively extensive exploited 1,4‐palladium migration process, the relevant 1,5‐Pd/H shift was far less investigated. We herein report a novel 1,5‐Pd/H shift pattern between a vinyl and an acyl group. Through the pattern, rapid access to 5‐membered‐dihydrobenzofuran and indoline derivatives has been achieved. Further studies have unveiled an unprecedented trifunctionalization (vinylation, alkynylation and amination) of a phenyl ring through 1,5‐palladium migration relayed decarbonylative Catellani type reaction. A series of mechanistic investigations and DFT calculations have provided insights into the reaction pathway. Notably, it was unveiled that the 1,5‐palladium migration in our case prefers a stepwise mechanism involving a PdIVintermediate.
Subject
General Chemistry,Catalysis
Cited by
4 articles.
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