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

C(sp(3))-C(sp(2)) cross-coupling reactions are an indispensable tool for organic synthesis. In these reactions transition metals have been extensively employed to promote the formation of valuable carbon-carbon bonds. Herein, 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 mild condition in the presence of a weak inorganic base. Preliminary mechanistic studies suggested a sulfonium ylide mechanism.

Automated summary

C(sp(3))-C(sp(2)) cross-coupling reactions are essential tools for organic synthesis. This study reports the discovery of a designer thioether as an effective catalyst for the reaction between an allyl bromide and an arylboronic acid.