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

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32 Cites (Scopus)

Resum

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 originalAnglès
Pàgines (de-a)8070-8076
Nombre de pàgines7
RevistaJournal of Organic Chemistry
Volum69
Número23
DOIs
Estat de la publicacióPublicada - 12 de nov. 2004
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