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

被引：1

作者：

Fouad, Manar Ahmed ^{[1
,2
]}

Ferretti, Francesco ^{[1
]}

Galie, Simone ^{[1
]}

Ragaini, Fabio ^{[1
]}

机构：

[1] Univ Milan, Dept Chem, Via C Golgi 19, I-20133 Milan, Italy

[2] Alexandria Univ, Fac Sci, Chem Dept, POB 426, Alexandria 21321, Egypt

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 38期

关键词：

homogeneous catalysis; formic acid; nitroarenes; nitrogen heterocycles; CO surrogates; DIELS-ALDER REACTION; CATALYZED ELECTROPHILIC AMINATION; ORGANIC NITRO-COMPOUNDS; OXYGEN-ATOM-TRANSFER; CARBON-MONOXIDE; PHENYL FORMATE; UNFUNCTIONALIZED DIENES; CARBONYLATION REACTIONS; CYCLIZATION; NITROSTYRENES;

D O I：

10.1002/ejoc.202300809

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页数：9

共 111 条

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