Reaction of diazonium salts with transition metals. Part 11. Palladium-catalyzed aryldesilylation of alkenylsilanes by arenediazonium salts

Abstract

Under palladium(0) catalysis, both (E)- and (Z)-RCHCHSiMe₃(RRh, 4-MeC₆H₄, 4-NO₂C₆H₄, n-C₆H₁₃, and MeOCH₂) were easily aryldesilylated by ArN₂X (ArPh, 4-MeC₆H₄, 4-BrC₆H₄ and 4-NO₂C₆H₄; XBF₄, PF₆, and Cl) to give (E)-RCHCHAr and RC(Ar)CH₂ as the main products at 25 °C in acetonitrile. anti- and syn-1,2-Elimination of Pd(0) and Me₃Si from the adducts, threo- and erythro-RCH(PdX)CHSiMe₃, generated from ArPdX and (E) and (Z)-RCHCHSiMe₃, respectively, are proposed for the formation of (E)-RCHCHAr from either isomer of RCHCHSiMe₃.