The α-trideuteromethylation of arylacetonitriles with deuterated methanol via deuterium autotransfer process catalyzed by a metal-ligand bifunctional iridium catalyst

Abstract

The development of deuterium incorporation techniques has become increasingly important for both academia and industry. Herein, a simple, general and efficient method for the α-trideuteromethylation of arylacetonitriles with CD3OD based on deuterium autotransfer process or deuterium-borrowing strategy was proposed and accomplished. In the presence of [Cp*Ir(2,2′-bpyO)(H2O)] and Cs2CO3 (0.3 equiv), a range of desirable products were obtained. The synthetic strategy is attractive due to easily available deuterium source, high atom efficiency and environmental friendliness. It was found that functional units in bpy ligand are crucial for the catalytic activity of iridium complexes. Furthermore, a DFT calculations and the synthetic application of this strategy were presented.