4.8 Article

Rhodium(I)-Catalyzed Addition of Arylboronic Acids to (Benzyl-/Arylsulfonyl)acetonitriles: Efficient Synthesis of (Z)-β-Sulfonylvinylamines and β-Keto Sulfones

Journal

ORGANIC LETTERS
Volume 13, Issue 2, Pages 208-211

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102598p

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Funding

  1. NSERC
  2. Merck Frosst Canada
  3. University of Toronto

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An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel beta-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful beta-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.

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