Manganese-catalysed HIE of Arenes and Heteroarenes

Abstract

Catalytic hydrogen isotope exchange (HIE) enables atom-economical deuterium incorporation into pharmacologically relevant molecules, typically with precious metal catalysts. The drive for increased sustainability and decreased environmental impact and physiological toxicity has piqued interest in the use of base-metals for catalytic HIE. The manganese complex [dmpe2MnH3] was applied as a catalyst to the HIE of furan and thiophene derivative using D2 as the deuterium source, however this system was incompatible with N-containing heterocycles. Development and application of the manganese hydride complex [dppbzMn(CO)3H] showed comparable reactivity to that of [dmpe2MnH3] for furan and thiophene derivatives, and enabled application to N-containing heteroarenes and carboarenes with increased functional group tolerance.