28686-98-8Relevant articles and documents
PALLADIUM-CATALYZED SYNTHESES OF BI- AND TER-THIOPHENES
Carpita, Adriano,Rossi, Renzo
, p. 575 - 584 (2007/10/02)
Several heteropolyaromatic compounds containing thiophen rings, of general formula 2, 3, and 5, which are possible antifungal agents, have been synthesized in good yields by Pd-catalyzed reactions.In particular, cross-coupling reactions between 2- or 3-thienylmagnesium bromide and dibromothiophens of general formula 8 in the presence of catalytic amounts of PdCl2, have been used to prepare three isomers (2a, 2b, and 2c) of the naturally occurring 2,2':5',2"-terthiophen, 1, as well as several bromobithienyls of general formula 3.An analogous procedure has been employed for the regioselective synthesis of 3'-bromo-2,2':5',2"-terthiophen, 4, starting from 2-thienylmagnesium bromide, 7a, and 2,3,5-tribromothiophen, 8.On the other hand, heterocyclic esters of general formula 5, which are not readily accessible using conventional organic methods, have been conveniently prepared by Pd-catalyzed ethoxycarbonylation of bromobithienyls 3 under mild experimental conditions.A short synthesis of 5'-(1-propynyl)-2,2'-bithienyl-5-carboxylic acid, 6, a compound isolated from the roots of Arctium lappa, shows the efficacy of the reported Pd-catalyzed reactions.