Arylsulfonyl fluoride boronic acids: Preparation and coupling reactivity

Abstract

We report the efficient and practical syntheses of ortho-, meta, and para-sulfonyl fluoride substituted benzene boronic acids. The syntheses of the para- and meta-isomers commence with the appropriate bromo-substituted benzenesulfonyl chlorides, and the ortho-isomer is prepared from benzenesulfonyl fluoride. The boronic acids undergo efficient Sukuki-Miyaura coupling reactions with a range of aryl halides. We also report an efficient Rh(I)-catalyzed conjugate addition reaction using the para-substituted boronic acid.