Trithiocarbonate Anion as a Sulfur Source for the Synthesis of 2,5-Disubstituted Thiophenes and 2-Substituted Benzo[b]thiophenes

Douglas B. Paixão, Daniel S. Rampon, Helena D. Salles, Eduardo G. O. Soares, Filipe N. Bilheri and Paulo H. Schneider*

*Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul, P.O. Box 15003, 91501-970, Porto Alegre, Rio Grande do Sul, Brazil, Email: paulosiq.ufrgs.br

D. B. Paixão, D. S. Rampon, H. D. Salles, E. G. O. Soares, F. N. Bilheri, P. H. Schneider, J. Org. Chem., 2020, 85, 12922-12934.

DOI: 10.1021/acs.joc.0c01516

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Abstract

Trithiocarbonate anions (CS₃^2-) can be generated in situ from CS₂ and KOH in dimethyl sulfoxide and used as a novel S^2- synthon for the synthesis of 2,5-disubstituted thiophenes from 1,3-butadiynes. In addition, this system was employed for a metal-free synthesis of 2-substituted benzo[b]thiophenes from 2-haloalkynyl (hetero)arenes.

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Key Words

thiophenes

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ID: J42-Y2020