Many different N-heterocycles can be prepared in high yields from suitably substituted nitroarenes in the presence of CO as a reductant [1], but the need for high-pressure CO lines have prevented a widespread use of these reactions. Here we report a general protocol for the preparation of N-heterocycles using phenyl formate as a practical CO surrogate. Indoles were mostly investigated, but the methodology was successfully extended to other heterocycles (carbazoles, quinolones, and oxazines). The desired compounds were obtained in yields often higher than those previously reported using gaseous CO. A cheap glass pressure tube can be employed as the reaction vessel. Mechanistic and kinetic analyses were successfully employed for clarifying both the decarbonylation reaction of phenyl formate and the cyclization mechanism.
Phenyl Formate: an Excellent CO Source for the Synthesis of Heterocycles from Nitroarenes / F.A.C. Ragaini, D. Formenti, F.M. Ferretti. ((Intervento presentato al 22. convegno EuCheMS Conference on Organometallic Chemistry tenutosi a Amsterdam nel 2017.
Phenyl Formate: an Excellent CO Source for the Synthesis of Heterocycles from Nitroarenes
F.A.C. Ragaini
Primo
;D. Formenti;F.M. Ferretti
2017
Abstract
Many different N-heterocycles can be prepared in high yields from suitably substituted nitroarenes in the presence of CO as a reductant [1], but the need for high-pressure CO lines have prevented a widespread use of these reactions. Here we report a general protocol for the preparation of N-heterocycles using phenyl formate as a practical CO surrogate. Indoles were mostly investigated, but the methodology was successfully extended to other heterocycles (carbazoles, quinolones, and oxazines). The desired compounds were obtained in yields often higher than those previously reported using gaseous CO. A cheap glass pressure tube can be employed as the reaction vessel. Mechanistic and kinetic analyses were successfully employed for clarifying both the decarbonylation reaction of phenyl formate and the cyclization mechanism.File | Dimensione | Formato | |
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