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; Paulo H Schneider

doi:10.1021/acs.joc.0c01516

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

J Org Chem. 2020 Oct 16;85(20):12922-12934. doi: 10.1021/acs.joc.0c01516. Epub 2020 Oct 1.

Authors

Douglas B Paixão¹, Daniel S Rampon², Helena D Salles¹, Eduardo G O Soares¹, Filipe N Bilheri¹, Paulo H Schneider¹

Affiliations

¹ Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul (UFRGS), P.O. Box 15003, 91501-970, Porto Alegre, Rio Grande do Sul, Brazil.
² Laboratório de Polímeros e Catálise (LAPOCA), Departamento de Química, Universidade Federal do Paraná (UFPR), P.O. Box 19061, 81531-990, Curitiba, Rio Grande do Sul, Brazil.

PMID: 32940466
DOI: 10.1021/acs.joc.0c01516

Abstract

The trithiocarbonate anion (CS₃^2-) was generated in situ from CS₂ and KOH in dimethyl sulfoxide by a simple method and used as a novel synthetic equivalent of the S^2- synthon for the synthesis of 2,5-disubstituted thiophenes from 1,3-butadiynes. Additionally, this system was employed for the metal-free synthesis of 2-substituted benzo[b]thiophenes from 2-haloalkynyl (hetero)arenes. These compounds were obtained from a cheap and readily available sulfur source in moderate to good yields, with good functional group tolerance.

Publication types

Research Support, Non-U.S. Gov't