THE PALLADIUM-CATALYZED "HEAD-TO-TAIL" CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH PHENYL OR 1-ALKENYL IODIDES. A NOVEL SYNTHESIS OF 2-PHENYL-1-ALKENES OR 2-ALKYL-1,3-ALKADIENES VIA ORGANOBORANES

Article abstract of DOI:10.1016/S0022-328X(00)82970-8

The reaction of phenyl or 1-alkenyl iodides with 1-alkenyl-1,3,2-benzodioxaboroles readily obtainable via the hydroboration of 1-alkynes, gives the corresponding "head-to-tail" cross-coupling products, 2-phenyl-1-alkenes or 2-alkyl-1,3-alkadienes, in good yields.The reaction is effectively catalyzed by catalytic amounts of palladium compounds in the presence of triethylamine.