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

Research output: Indexed journal article Articlepeer-review

32 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8070-8076
Number of pages7
JournalJournal of Organic Chemistry
Volume69
Issue number23
DOIs
Publication statusPublished - 12 Nov 2004
Externally publishedYes

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