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Palladium‐Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles
Author(s) -
ElAtawy Mohamed A.,
Ferretti Francesco,
Ragaini Fabio
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700165
Subject(s) - chemistry , palladium , intramolecular force , catalysis , intramolecular reaction , combinatorial chemistry , organic chemistry
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).