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The direct reductive N -arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P -oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N -methylanilines from various stable isotopologues of nitromethane (i.e., CD 3 NO 2 , CH 3  15 NO 2 , and 13 CH 3 NO 2 ), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.

P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C–N Coupling with Nitromethane as a Methylamine Surrogate