Organoboranes. 56. Systematic study of the reactions of 1-alkenylboronic esters with representative organolithium and grignard reagents to provide an efficient, selective synthesis of organyl-1-alkenylborinic esters

Article abstract of DOI:10.1021/om00028a021

A selective reaction of the ate complexes formed with 1-alkenylboronic esters and organolithium or Grignard reagents, by treatment with either Br?nsted or Lewis acids at -78 °C to give the corresponding organylalkenylborinic esters, is explored in this study. This systematic, detailed study reveals that the nature of the alkoxy group on boron, the nature and the amount of the alkyllithium or Grignard reagent used, the solvent, the reaction temperature, and the nature and amount of the acid used all play significant roles in influencing both the yield and the selectivity achieved for the formation of the desired organylalkenylborinates. Optimized procedures for the syntheses of representative organylalkenylborinic esters in high yield are summarized.