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 [Ar2SCF3](+)[OTf](-) provided the arylation products (R-Ar) in good to high yields. The reaction confirms that the S-Ar bonds of [Ar2SCF3](+)[OTf](-) can be readily cleaved in the presence of Pd complexes. The relatively electron-poor aryl groups of asymmetric [(ArArSCF3)-Ar-1-S-2](+)[OTf](-) salts are more favorably transferred compared to the electron-rich ones. This reaction represents the first report of utilization of [Ar2SCF3](+)[OTf](-) as arylation reagents in organic synthesis.