2026-08-31T12:50:08Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/45302021-11-10T09:38:25Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Synthesis of Functionalized 1H-Indenes and Benzofulvenes through Iodocyclization of o-(Alkynyl)styrenes García García, Patricia Sanjuán Cortázar, Ana María Rashid, Muhammad A. Martínez Cuezva, Alberto Fernández Rodríguez, Manuel A. Rodríguez, Félix Sanz Díez, Roberto Química orgánica Chemistry, Organic A convenient method for the preparation of synthetically useful 3- iodoindene derivatives has been developed. This protocol, based on the 5-endo iodocyclization reaction of o-(alkynyl)styrenes, represents one of the scarce examples of halocyclizations using olefins as nucleophilic counterparts and allows the synthesis of both 3-iodo-1H-indenes (from β-alkyl-β-alkyl/aryl-o-(alkynyl)styrenes) and 3-iodobenzofulvenes (from β,β-diaryl-o-(alkynyl)styrenes) in good yields under mild reaction conditions. In addition, related alkoxyiodocyclization processes are described, which are particularly interesting in their intramolecular version because they allow the synthesis of heteropolycyclic structures containing the indene core. Finally, the usefulness of the prepared 3-iodoindenes has been demonstrated by the synthesis of several polysubstituted indene derivatives through conventional palladium-catalyzed cross-coupling reactions and iodine−lithium exchange processes. Ministerio de Economiá y Competitividad (MINECO) and FEDER (CTQ2013-48937- C2-1P) and Junta de Castilla y León (BU237U13 and BU076U16) 2017-07-13T11:36:37Z 2018-01-20T03:45:07Z 2017-01 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 0022-3263 http://hdl.handle.net/10259/4530 10.1021/acs.joc.6b02788 eng JOC, Journal of Organic Chemistry. 2017, V. 82, n. 2, p. 1155–1165 http://dx.doi.org/10.1021/acs.joc.6b02788 info:eu-repo/semantics/openAccess application/pdf American Chemical Society https://riubu.ubu.es/bitstream/10259/4530/4/Garc%c3%ada-JOC_2017.pdf.jpg Hispana TEXT http://rightsstatements.org/vocab/CNE/1.0/ RIUBU. Repositorio Institucional de la Universidad de Burgos http://hdl.handle.net/10259/4530