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An unexpected palladium migration from vinylic sp2 carbon to allylic sp3 carbon

  • Letter
  • Organic Chemistry
  • Published:
Chinese Science Bulletin

Abstract

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.

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Authors and Affiliations

  1. Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, Beijing, 100871, China

    BiJie Li & ZhangJie Shi

  2. China and State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    ZhangJie Shi

Authors
  1. BiJie Li
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  2. ZhangJie Shi
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Correspondence to ZhangJie Shi.

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Li, B., Shi, Z. An unexpected palladium migration from vinylic sp2 carbon to allylic sp3 carbon. Chin. Sci. Bull. 55, 2807–2810 (2010). https://doi.org/10.1007/s11434-010-4034-2

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  • DOI: https://doi.org/10.1007/s11434-010-4034-2

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