4.8 Article

Cobalt-Catalyzed Allylation of Amides with Styrenes Using DMSO as Both the Solvent and the α-Methylene Source

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ORGANIC LETTERS
卷 21, 期 18, 页码 7248-7253

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02462

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资金

  1. NSFC [81502909, 21502100, 21877020]
  2. Guangdong Natural Science Funds for Distinguished Young Scholar [2017A030306031]
  3. Science and Technology Programs of Guangdong Province [2015B020225006]
  4. Medical Scientific Research Foundation of Guangdong Province [A2018421]
  5. Natural Science Foundation Research Team of Guangdong Province [2018B030312001]

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An efficient synthesis of privileged allylic amines has been developed via cobalt-catalyzed allylation of amides with styrenes, in which DMSO was used as both the solvent and the alpha-methylene source. This transformation features high yields, and selectivity for the (E)-isomer of the linear product. Through the experimental and computational investigations, a sequential K2S2O8-mediated oxidative coupling/cobalt-assisted regioselective alkene insertion/beta-H elimination/alkene dissociation/hydride transfer process has also been deduced.

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