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Título : Synthesis of Functionalized 1H-Indenes and Benzofulvenes through Iodocyclization of o-(Alkynyl)styrenes
Autor : García García, Patricia
Sanjuán Cortázar, Ana María
Rashid, Muhammad A.
Martínez Cuezva, Alberto
Fernández Rodríguez, Manuel A.
Rodríguez, Félix
Sanz Díez, Roberto
Publicado en: JOC, Journal of Organic Chemistry. 2017, V. 82, n. 2, p. 1155–1165
Editorial : American Chemical Society
Fecha de publicación : ene-2017
Fecha de disponibilidad: 20-ene-2018
ISSN : 0022-3263
DOI: 10.1021/acs.joc.6b02788
Resumen : 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.
Materia: Química orgánica
Chemistry, Organic
URI : http://hdl.handle.net/10259/4530
Versión del editor: http://dx.doi.org/10.1021/acs.joc.6b02788
Aparece en las colecciones: Artículos SINTORG

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