Palladium-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Organic Triflates

Article abstract of DOI:10.1021/jo00060a041

The cross-coupling reaction of 9-alkyl-9-borabicyclo<3.3.1>nonane (9-R-9-BBN), 1-alkenyl-1,3,2-benzodioxaborole, or aryl boronic acid with 1-alkenyl or aryl triflates in the presence of K3PO4 (1.5 equiv) and a catalytic amount of Pd(PPh3)4 or Cl2Pd(dppf) resulted in high yields.The reaction conditions are sufficiently mild so that a variety of functionalized alkenes, alkadienes, and arenes are readily obtained.The utility of the present reaction was demonstrated by the cyclization of ω-alkenyl triflates leading to a benzo-fused cycloalkene and bicyclic alkene via a hydroboration intramolecular coupling sequence.