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An unexpected palladium migration from vinylic sp^2 carbon to allylic sp^3 carbon

An unexpected palladium migration from vinylic sp^2 carbon to allylic sp^3 carbon
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摘要 A unique transformation to realize the allylic amination from vinylic bromides was described and an unexpected C-Pd migration was observed from sp2 carbon to adjacent allylic sp3 carbon initiated from vinyl bromide. Various 3-aryl-2-bromopropenes and secondary amines were surveyed and the allyl amination products were obtained in moderate isolated yields. The primary amine was not fit for this transformation. Mechanistic studies indicate that this migration went through β-hydride elimination and reverse C=C bond insertion. A unique transformation to realize the allylic amination from vinylic bromides was described and an unexpectecl C-Pd migranon was observed from sp2 carbon to adjacent allylic sp3 carbon initiated from vinyl bromide. Various 3-aryl-2-bromopropenes and secondary amines were surveyed and the allyl arnination products were obtained in moderate isolated yields. The primary amine was not fit for this transformation. Mechanistic studies indicate that this migration went through β-hydride elimination and reverse C=C bond insertion.
出处 《Chinese Science Bulletin》 SCIE EI CAS 2010年第25期2807-2810,共4页
基金 supported by Peking University,the National Natural Science Foundation of China (20542001 and 20521202) the National Basic Research Program of China (2009CB825300)
关键词 SP3 SP2 碳烯 迁移 烯丙基 溴乙烯 乙烯基 palladium migration, allylic amination
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参考文献17

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