Highly Regio- and Stereoselective Palladium(0)-Catalyzed Addition of Organoboronic Acids with 1,2-Allenic Sulfones, Sulfoxides, or Alkyl- or Aryl-Substituted Allenes in the Presence of Acetic Acid: An Efficient Synthesis of E-Alkenes

Abstract

Two sets of reaction conditions were established to enable the palladium(0)-catalyzed addition of organoboronic acids with 1,2-allenic sulfones, sulfoxides, or alkyl- or aryl-substituted allenes in the presence of acetic acid. This reaction provides a new way for the stereoselective synthesis of tri- or tetrasubstituted E-alkenes. With arylboronic acids, the reactions of 1,2-allenic sulfones, sulfoxides, and alkyl-substituted allenes gave only 1-12% of specific regioisomers; the reactions of aryl-substituted allenes afforded only E-alkenes in very high regioselectivity.

allenes - sulfones - sulfoxides - palladium - addition reactions - boron

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