Regioselective deuteration of alcohols in D2O catalysed by homogeneous manganese and iron pincer complexes

Abstract

We report a convenient and cost-effective protocol for the regioselective deuteration of primary and secondary alcohols using Earth abundant homogeneous first row transition metal pincer catalysts. D₂O is utilized as both a deuterium source and a solvent, allowing for a benign inexpensive process. Depending on the metal selected (Mn or Fe), a high degree of deuterium incorporation was observed selectively either at the α and β position (Mn) or exclusively at the α position (Fe), for primary alcohols. This simple, efficient, and cost-effective protocol for alcohol C–H bond deuteration constitutes a powerful tool for the large scale synthesis of deuterated molecules.