A Thioether-Catalyzed Cross-Coupling Reaction of Allyl Halides and Arylboronic Acids.

Csp3-Csp2 cross-coupling reactions are an indispensable tool for organic synthesis, in which transition metals have been extensively employed to promote the formation of valuable carbon-carbon bonds. In this article, we report our recent discovery of a designer thioether as a highly active organocatalyst for reactions between an allyl bromide and an arylboronic acid. The cross-coupling event occurred readily under a mild condition in the presence of a weak inorganic base. Preliminary mechanistic studies suggested a sulfonium ylide mechanism.