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  • A practical, one-pot synthesis of highly substituted thiophenes and benzo[b]thiophenes from bromoenynes and o-alkynylbromobenzenes.

A practical, one-pot synthesis of highly substituted thiophenes and benzo[b]thiophenes from bromoenynes and o-alkynylbromobenzenes.

Organic letters (2011-09-03)
Verónica Guilarte, Manuel A Fernández-Rodríguez, Patricia García-García, Elsa Hernando, Roberto Sanz
RESUMEN

An efficient synthesis of thiophenes and benzo[b]thiophenes has been developed from easily available bromoenynes and o-alkynylbromobenzene derivatives. This novel one-pot procedure involves a Pd-catalyzed C-S bond formation using a hydrogen sulfide surrogate followed by a heterocyclization reaction. Moreover, in situ functionalization with selected electrophiles further expands the potential of this methodology to the preparation of the corresponding highly substituted sulfur heterocycles.

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Sigma-Aldrich
Bromobenzene, ≥99.5% (GC)
Sigma-Aldrich
Bromobenzene, ReagentPlus®, 99%