A Practical, One-Pot Synthesis of Highly Substituted Thiophenes and Benzo[<i>b</i>]thiophenes from Bromoenynes and <i>o</i>-Alkynylbromobenzenes

Abstract

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.