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You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content. Variation 2: Reduction with Chromium(II)/Manganese(0)

DOI: 10.1055/sos-SD-031-01870

Chiara, J. L.Science of Synthesis, (2007311707.

The reduction of nitroarenes with catalytic chromium(II) chloride in the presence of excess manganese metal and chlorotrimethylsilane in dimethylformamide at room temperature provides N,N-bis(trimethylsilyl)arylamines, which are subsequently converted to the corresponding arylamines by stirring with aqueous dimethylformamide (Scheme 13).[‌55‌‌57‌] This reaction tolerates a wide range of substituents on the aromatic ring, and it has been successfully applied to solid-supported nitroarenes [e.g., 27, from which anilinium salt 29 is synthesized via bis(trimethylsilyl)arylamine 28].[‌58‌]

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