2024-03-29T12:48:50Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/45302021-11-10T09:38:25Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
2018-01-20T03:45:07Z
urn:hdl:10259/4530
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
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.
2017-07-13T11:36:37Z
2018-01-20T03:45:07Z
2017-01
info:eu-repo/semantics/article
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
American Chemical Society