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oai:riubu.ubu.es:10259/39092021-11-10T09:38:19Zcom_10259_3593com_10259_5086com_10259_2604com_10259_3924col_10259_3594col_10259_3925

A Practical, One-Pot Synthesis of Highly Substituted Thiophenes and Benzo[b]thiophenes from Bromoenynes and o-Alkynylbromobenzenes Guilarte Moreno, Verónica Fernández Rodríguez, Manuel A. García García, Patricia Hernando Santa Cruz, Elsa Sanz Díez, Roberto Química orgánica Chemistry, Organic Chemistry, Organic 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. Junta de Castilla y Leon (BU021A09 and GR-172) and Ministerio de Ciencia e Innovacion (MICINN) and FEDER (CTQ2010-15358 and CTQ2009-09949/BQU) for financial support. P.G.-G. and M.A.F.-R. thank MICINN for "Juan de la Cierva" and "Ramon y Cajal" contracts Junta de Castilla y Leon (BU021A09 and GR-172) and Ministerio de Ciencia e Innovacion (MICINN) and FEDER (CTQ2010-15358 and CTQ2009-09949/BQU) for financial support. P.G.-G. and M.A.F.-R. thank MICINN for "Juan de la Cierva" and "Ramon y Cajal" contracts This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. 2016-01-21T09:51:47Z 2016-01-21T09:51:47Z 2011-09 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1523-7060 http://hdl.handle.net/10259/3909 10.1021/ol201970m eng Organic Letters. 2011. V. 13, n. 19, p. 5100-5103 http://dx.doi.org/10.1021/ol201970m info:eu-repo/grantAgreement/MICINN/CTQ2010-15358 info:eu-repo/grantAgreement/MICINN/CTQ2009-09949/BQU info:eu-repo/grantAgreement/JCyL/BU021A09 info:eu-repo/grantAgreement/JCyL/GR-172 info:eu-repo/semantics/openAccess application/pdf American Chemical Society https://riubu.ubu.es/bitstream/10259/3909/4/Guilarte_OL_2011.pdf.jpg Hispana TEXT http://rightsstatements.org/vocab/CNE/1.0/ RIUBU. Repositorio Institucional de la Universidad de Burgos http://hdl.handle.net/10259/3909