Palladium-catalyzed reaction of boronic acids with chiral and racemic alpha-bromo sulfoxides.
Palladium-catalyzed cross-coupling reactions of racemic alpha-bromo sulfoxides with boronic acids are carried out in either aqueous or nonaqueous medium with formation of a new C sp(3)-C sp(2) bond. The arylation of chiral alpha-bromo sulfoxides occurs without racemization. The cross-coupling reaction is general and gives high yields with arylboronic acids substituted with either donor or acceptor groups but gives poor results with heteroarylboronic acids. The best yields are obtained using degassed solvents and CsF instead of aqueous base. The use of aqueous base and the presence of oxygen favor the homocoupling side reaction.
Rodríguez
Nuria
N
Departamento de Química Orgánica, Universidad de Valencia, Avda. Vicent Andres Estelles s/n, 46100 Burjassot, Spain.
Cuenca
Ana
A
Ramírez de Arellano
Carmen
C
Medio-Simón
Mercedes
M
Peine
Denissa
D
Asensio
Gregorio
G