In the presence of carbon monoxide, the palladium/phenanthroline system catalyzes the intramolecular amination of thiophene rings following the reduction of a nitroalkene moiety directly attached to the S-heterocyclic ring. Optimization of the ligand and reaction conditions allowed the synthesis of a series of thienopyrroles aryl/alkyl-substituted at either the 2- or 3-position of the pyrrole ring. By using low pressures of carbon monoxide (5 bars), high yields of fused bicyclic compounds have been obtained (up to 98 % yield).
Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes : Synthesis of Thienopyrroles / M.A. Elatawy, F. Ferretti, F. Ragaini. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2017:14(2017 Apr), pp. 1902-1910. [10.1002/ejoc.201700165]
Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes : Synthesis of Thienopyrroles
M.A. Elatawy;F. Ferretti;F. Ragaini
2017
Abstract
In the presence of carbon monoxide, the palladium/phenanthroline system catalyzes the intramolecular amination of thiophene rings following the reduction of a nitroalkene moiety directly attached to the S-heterocyclic ring. Optimization of the ligand and reaction conditions allowed the synthesis of a series of thienopyrroles aryl/alkyl-substituted at either the 2- or 3-position of the pyrrole ring. By using low pressures of carbon monoxide (5 bars), high yields of fused bicyclic compounds have been obtained (up to 98 % yield).File | Dimensione | Formato | |
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