REACTION OF DIAZONIUM SALTS WITH TRANSITION METALS XII. PALLADIUM-CATALYZED ARYLDESTANNYLATION OF α-STYRYLSTANNANES BY ARENEDIAZONIUM SALTS

Article abstract of DOI:10.1016/0022-328X(86)80264-9

Under palladium(0) catalysis, Ph(R3Sn)C=CH2 (R=Me, Et and Bu) easily reacted with ArN2BF4 (Ar=XPh, X=H, 4-Me, 4-I, 4-MeCO, 4-EtOCO, 3-NO2 and 4-NO2) and selectively produced (Z)-PhCH=CHAr but not Ph(Ar)C=CH2.An addition-elimination mechanism instead of the transmetallation from tin to palladium is postulated for this unusual regiochemistry.