STEREOCHEMISTRY OF REACTION OF (E)- AND (Z)-β-TRIMETHYLSILYLSTYRENE WITH ARYLPALLADIUM TETRAFLUOROBORATES GENERATED FROM ARENEDIAZONIUM TETRAFLUOROBORATES AND PALLADIUM(0)

Abstract (E)- and (Z)-PhCH=CHSiMe3 react easily with [ArPd]+BF4− to give (E)-PhCH=CHAr and Ph(Ar)C=CH2 at 25 °C. Stereochemistry of the desilylation is disclosed by using (E)- and (Z)-PhCH=CDSiMe3, that is, syn-addition of Ar-Pd species followed by anti-elimination of Pd and Me3Si moiety for (E)-isomer and syn-elimination for (Z)-isomer are proposed.