Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content.
31.30.1.11.2 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]

Meeeee 88 Meeeeeeee Meeeeeeeee ee e Meeeeeeeee eeee Meeeeeee(MM)/Meeeeeeee(8)[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeee Meeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Meeee 88 eee eeeeeeee ee eeeeeeee[‌88‌] eeee Meee eeeee eeeee (88ee, 8.88eeee·e8). Me eee eeeeeeeeee eeeeee eee eeeee. Me eeee eeeee ee eee MMM eeee eeeee MeMe8 (8ee, 8.888eeee) eee Me (88ee, 8.8eeee). MMMMe (88.8ee, 8.8eeee) eee eeee eeeee, eee eee eeeeeee eee eeeeee eeeeeeeee. Mee eeeee, eeeee eeeeeee ee eee ee eee Me, eee eeee eeeeeeeee eeeeeeeeeee ee e eeeeeeeeeeeee eeee eee eeeeeeeeee eeeeee eeee MMM, MeMM, eee MM8Me8. Mee eeeeeeeee eee eeeeeee eeee eee eeeee ee eeeeeeeee eeee MMM/MM8Me8 (88:8). Mee eeeee eee eeeeeeee eee eee eeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee 88; eeeee: 8.8ee (88%).

References