Several ortho-nitrobiarenes and dinitrobiarenes were submitted to Ru3(CO)12-catalyzed reductive carbonylation in acetonitrile and in cis-cyclooctene. The main reaction products were the corresponding amines and five-membered heterocycles such as indoles and imidazoles. Small amounts of six-membered cyclization products such as acridane dimers, phenothiazine, quinoxalines were also found. The cyclization to indole occurred also at room temperature under irradiation or with zinc. The use of cis-cyclooctene as the solvent also trapped the nitroso intermediates. Nitrones were formed in this reaction and were suggested to be intermediate in certain cyclizations. Force-field calculations allowed to suggest organoruthenium intermediates in these reactions.

Triruthenium dodecacarbonyl-catalized reductive carbonylation of nitroarenes: cyclization, carbon monoxide insertion and reduction : An overview / A. Bassoli, S. Cenini, F. Farina, M. Orlandi, B. Rindone. - In: JOURNAL OF MOLECULAR CATALYSIS. - ISSN 0304-5102. - 89:1-2(1994), pp. 121-142.

Triruthenium dodecacarbonyl-catalized reductive carbonylation of nitroarenes: cyclization, carbon monoxide insertion and reduction : An overview

A. Bassoli
Primo
;
S. Cenini
Secondo
;
1994

Abstract

Several ortho-nitrobiarenes and dinitrobiarenes were submitted to Ru3(CO)12-catalyzed reductive carbonylation in acetonitrile and in cis-cyclooctene. The main reaction products were the corresponding amines and five-membered heterocycles such as indoles and imidazoles. Small amounts of six-membered cyclization products such as acridane dimers, phenothiazine, quinoxalines were also found. The cyclization to indole occurred also at room temperature under irradiation or with zinc. The use of cis-cyclooctene as the solvent also trapped the nitroso intermediates. Nitrones were formed in this reaction and were suggested to be intermediate in certain cyclizations. Force-field calculations allowed to suggest organoruthenium intermediates in these reactions.
carbon monoxide; carbonylation; cyclization; nitroarenes; ruthenium
Settore CHIM/06 - Chimica Organica
Settore CHIM/03 - Chimica Generale e Inorganica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/177966
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