期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 38, 页码 16205-16210出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c08035
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资金
- NIH NIGMS [GM114547]
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., CD3NO2, (CH3NO2)-N-15, and (CH3NO2)-C-13), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.
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