Palladium-catalyzed reaction of boronic acids with chiral and racemic α-bromo sulfoxides

Nuria Rodríguez, Ana Cuenca, Carmen Ramírez De Arellano, Mercedes Medio-Simón, Denissa Peine, Gregorio Asensio

Producción científica: Artículo en revista indizadaArtículorevisión exhaustiva

32 Citas (Scopus)

Resumen

Palladium-catalyzed cross-coupling reactions of racemic α-bromo sulfoxides with boronic acids are carried out in either aqueous or nonaqueous medium with formation of a new C sp3-C sp2 bond. The arylation of chiral α-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.

Idioma originalInglés
Páginas (desde-hasta)8070-8076
Número de páginas7
PublicaciónJournal of Organic Chemistry
Volumen69
N.º23
DOI
EstadoPublicada - 12 nov 2004
Publicado de forma externa

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