The palladium-catalyzed C–N cross coupling of
sulfinamides
and aryl halides is reported. In the presence of Pd2(dba)3, tBuXPhos, NaOH, and a small amount of water,
the C–N cross coupling of chiral tert-butanesulfinamide
and aryl halides was accomplished to give N-aryl tert-butanesulfinamide without racemization, and the coupling
of racemic p-toluenesulfinamide smoothly afforded N-aryl p-toluenesulfinamides. 2-Bromopyridine
was also suitable for the coupling. Addition of a small amount of
water to the catalytic system was of importance to obtain high yields.