Reductive deuteration of ketones, benzhydrols, α,β-unsaturated ketones, and aryl alkenes by deuterium iodide in acetic acid

Reduction of substituted benzophenones, benzhydrols, diaryl alkenes, and benzylideneacetophenones with D3PO2 in DOAc in the presence of a small amount of iodine results in reduction to the corresponding alkanes efficiently, relatively inexpensively, and with regioselective incorporation of deuterium. Isotopic exchange results in incorporation of more than the expected amount of deuterium with the last two classes of compound.