Palladium-Catalyzed Arylation of Arylboronic Acids with Yagupolskii-Umemoto Reagents.

A Pd-catalyzed Suzuki cross-coupling of arylboronic acids with Yagupolskii-Umemoto reagents was explored. In contrary to trifluoromethylations, the Pd-catalyzed reaction of R-B(OH)2 and Ar2 SCF3 OTf provided the arylation products (R-Ar) in good to high yields. The reaction confirms that the S-Ar bonds of Ar2 SCF3 OTf can be readily cleaved in the presence of Pd complexes. The relatively electron-poor aryl groups of asymmetric Ar(1) Ar(2) SCF3 OTf salts are more favorably transferred compared to the electron-rich ones. This reaction represents the first report of utilization of Ar2 SCF3 OTf as arylation reagents in organic synthesis.