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

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....

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Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (19), p.5100-5103
Main Authors: Guilarte, Verónica, Fernández-Rodríguez, Manuel A, García-García, Patricia, Hernando, Elsa, Sanz, Roberto
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Alkynes - chemistry
Bromobenzenes - chemistry
Molecular Structure
Thiophenes - chemical synthesis
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201970m