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Paper | Special issue | Vol 30, No. 1, 1990, pp.645-658
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S90
Convenient Synthesis of Various Terheterocyclic Compounds by Pd(0)-Catalyzed Coupling Reactions

Salo Gronowitz* and Dan Peters

*Organic Chemistry 1 Chemical Center, University of Lund, P. O. Box 124, SE-221 00, Lund, Sweden

Abstract

Various terheterocyclic compounds containing thiophene, furan, selenophene, pyridine, and thiazole rings have been obtained by the Pd(PPh3)4-catalyzed coupling of dihalo-substituted heterocyclic compounds with heterocyclic boronic acids, using sodium bicarbonate as base and a 1,2-dimethoxyethane - water mixture as solvent. In case when the boronic acids were not available or easily deboronated, and/or the heterocyclic halo derivatives were unstable in alkalone solution, trialkylstannylheterocyclies were used instead of boronic acids in the coupling with dihaloheterocycles, with THF as solvent and PdCl2(PPh3)2 as catalyst. The naturally occuring 3’-methoxy-2,2’:5’,2"-terthiophene was prepared by a copper-promoted nucleophilic substitution of 3’-iodo-2,2’:5’,2"-terthiophene, previously prepared by Pd(0)-catalyzed coupling of 2,3,5-triiodothiophene with 2-thiophene boronic acid.