Reactions of alkynes with trisubstituted (Z)-bromoalkenyl-pinacolboronates towards the synthesis of 1,2,4,6-tetrasubstituted benzenes

Treatment of trisubstituted (Z)-bromoalkenyl-pinacolboronates with terminal alkynes in the presence of cuprous iodide, palladium(0) tetrakis(triphenylphosphine) and Hünig’s base leads to the formation of 1,2,4,6-tetrasubstituted aromatic compounds in a one-pot fashion. Substrate scope was shown for three trisubstituted (Z)-bromoalkenyl-pinacolboronates and four terminal alkynes.