Molybdenum-mediated reductive deuteration of nitroarenes with D2O: synthesis of ortho- and para-deuterated anilines

Abstract

A unique and practical molybdenum-mediated reductive deuteration of nitroarenes for the selective synthesis of ortho- and para-deuterated anilines has been developed. Using Mo(CO)₆ as the reductant and the catalyst and D₂O as a cheap and operationally convenient D-source, a range of deuterated anilines were prepared from the corresponding nitroarenes with high yields and reliable deuteration levels. High regioselectivity was observed where deuterium incorporation took place selectively at the ortho- and para-positions. Notably, functional groups such as ether, thioether, acetyl and halides were compatible in this reaction without affecting the regioselectivity.