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- Title
Use of Formic Acid as a CO Surrogate for the Reduction of Nitroarenes in the Presence of Dienes: A Two‐Step Synthesis of N‐Arylpyrroles via 1,2‐Oxazines.
- Authors
Fouad, Manar Ahmed; Ferretti, Francesco; Galiè, Simone; Ragaini, Fabio
- Abstract
Formic acid, activated by acetic anhydride and a base, was employed as a CO surrogate to deoxygenate nitroarenes to nitrosoarenes, a reaction catalyzed by a palladium/phenanthroline complex in the homogeneous phase. Nitrosoarenes were trapped by conjugated dienes to give 3,6‐dihydro‐2H‐[1,2]‐oxazines. The latter were then transformed into N‐arylpyrroles employing CuCl as the catalyst. The reaction was designed to give the best results for pyrroles lacking any substituent in the 2 and 5 positions, which are difficult to produce employing most pyrrole syntheses.
- Subjects
NITROAROMATIC compounds; FORMIC acid; DIOLEFINS; OXAZINES; ACETIC anhydride; PHENANTHROLINE; PYRROLES
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 38, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300809