Tandem synthesis of N -methylated tertiary amines via three-component coupling of carbonyl compounds, amines, and methanol.

An Ir-catalyzed tandem synthesis of various N -methylated tertiary amines from three-component coupling of carbonyl compounds, amines, and methanol following reductive amination/ N -methylation is reported for the first time. A wide array of substrates with tolerance of different functional groups was demonstrated. The protocol was extended to the synthesis of N -methyl containing pharmaceutically important drug molecules. A probable catalytic cycle was proposed based on various control experiments and different analytical techniques such as NMR, IR and ESI-MS.