Alkali Metal Amide-Catalyzed α-Deuteration of Sulfides

The catalytic α-deuteration of sulfides was developed under mild conditions by using alkali metal amides [KN(SiMe 3 ) 2 and CsN(SiMe 3 ) 2 ] as the catalyst. This approach successfully achieves a selective and efficient H/D exchange reaction of sulfides with D 2 without using transition metal catalysts. A series of deuterium-labeled thioanisoles and alkyl methyl sulfides were obtained in good to high levels of deuterium incorporation.