4.5 Article

Ligand-dependent stereoselective Suzuki-Miyaura cross-coupling reactions of β-enamido triflates

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 17, Issue -, Pages 2657-2662

Publisher

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.17.179

Keywords

enamides; isomerization; Suzuki-Miyaura coupling; vinyl triflates

Funding

  1. Czech Academy of Sciences [RVO: 61388963]
  2. Ministry of Education, Youth and Sports in the program INTER-EXCELLENCE [LTAUSA18037]

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The stereoselective Suzuki-Miyaura cross-coupling of (Z)-beta-enamido triflates is demonstrated, showing different retention or inversion of configuration in the synthesis of beta,beta-diaryl-substituted enamides depending on the ligand in the palladium catalyst. This method provides access to both isomers of the target enamides from (Z)-beta-enamido triflates.
The stereoselective Suzuki-Miyaura cross-coupling of (Z)-beta-enamido triflates is demonstrated. Depending on the nature of the ligand in the palladium catalyst, either retention or inversion of the configuration during the synthesis of beta,beta-diaryl-substituted enamides is observed. Thus, the method provides synthetic access to both isomers of the target enamides from (Z)-beta-enamido triflates.

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