The reductive cyclization of different organic nitro compounds by carbon monoxide, catalyzed by transition metal complexes, is a very efficient and clean strategy for the synthesis of many N-heterocycles. However, it requires the use of autoclaves and pressurized CO lines. In this pa-per, the authors will present the results obtained in their laboratories on the use of phenyl for-mate as a convenient CO surrogate, able to liberate carbon monoxide under reaction conditions and allowing for the use of a cheap glass pressure tube as a reaction vessel. In most cases, yields were better than those previously reported using pressurized CO, proving that the use of CO surrogates can be a viable alternative to the gaseous reagent.

Use of Phenyl Formate as a CO Surrogate for the Reductive Cyclization of Organic Nitro Compounds to Yield Different N-Heterocycles: Avoiding the Use of Autoclaves and Pressurized Gases / F.A.C. Ragaini, F.M. Ferretti, M.A.F. Abdellatif. - In: CHEMISTRY PROCEEDINGS. - ISSN 2673-4583. - 12:1(2022 Nov 18), pp. 85.1-85.7. [10.3390/ecsoc-26-13711]

Use of Phenyl Formate as a CO Surrogate for the Reductive Cyclization of Organic Nitro Compounds to Yield Different N-Heterocycles: Avoiding the Use of Autoclaves and Pressurized Gases

F.A.C. Ragaini
Primo
;
F.M. Ferretti
Penultimo
;
M.A.F. Abdellatif
Ultimo
2022

Abstract

The reductive cyclization of different organic nitro compounds by carbon monoxide, catalyzed by transition metal complexes, is a very efficient and clean strategy for the synthesis of many N-heterocycles. However, it requires the use of autoclaves and pressurized CO lines. In this pa-per, the authors will present the results obtained in their laboratories on the use of phenyl for-mate as a convenient CO surrogate, able to liberate carbon monoxide under reaction conditions and allowing for the use of a cheap glass pressure tube as a reaction vessel. In most cases, yields were better than those previously reported using pressurized CO, proving that the use of CO surrogates can be a viable alternative to the gaseous reagent.
nitroarenes; nitroalkenes; indoles; carbazoles; oxazines; palladium; carbon monoxide; CO sur-rogate; homogeneous catalysis; carbonylation reactions;
Settore CHIM/03 - Chimica Generale e Inorganica
Settore CHIM/06 - Chimica Organica
   Piano di Sostegno alla Ricerca 2015-2017 - Linea 2 "Dotazione annuale per attività istituzionali" (anno 2020)
   UNIVERSITA' DEGLI STUDI DI MILANO
18-nov-2022
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/956742
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