Desulfurative Deuteration of (Hetero)Aryl Sulfides With D2O by Nickel Catalysis.

Selective deuteration of (hetero)aryl rings is of great significance and interest, yet it has remained a challenge, especially when employing D2O as deuterium source. Herein, the selective desulfurative deuteration of widely available (hetero)aryl sulfides with D2O (mostly 1.5 or 3.0 equiv.) has been established by nickel catalysis. This strategy affords an efficient and robust route for the synthesis of a wide range of deuterated (hetero)arenes (87 examples, > 10 different heterocycles) in generally good yields and high deuterium incorporation with good functional group compatibility. The catalytic reaction could be applied to scaled-up synthesis (e.g., 6.4 g for product 2, 0.1 mol% Ni catalyst, 590 TON) and late-stage deuteration of various drugs and bioactive molecules.