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.

Key words

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

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13

Crystal structure data for (E)-4ca: C₁₉H₂₂O₂S, MW = 314.43, triclinic, space group P-1, Mo Kα, final R indices [I > 2σ(I)], R1 = 0.0464, w R2 = 0.1016, a = 9.56611 (11) Å, b = 9.9879 (11) Å, c = 10.6025 (12) Å, α = 102.675 (2)°, β = 101.020 (2)°, γ = 116.035 (2)°, V = 838.98 (16) ų, T = 293 (2) K, Z = 2, reflections collected/unique: 5004/3565 (R _int = 0.0485), no observation [I > 2σ(I)] 3565, parameters 234. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Centre under CCDC 613372.