2026-04-29T08:21:04Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/42782022-04-29T12:02:48Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Brønsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration
Álvarez Manuel, Estela
Nieto Faza, Olalla .
Silva López, Carlos
Fernández Rodríguez, Manuel A.
Sanz Díez, Roberto
benzofulvenes
Brønsted acid
catalysis
indolemigration
Nazarov cyclization
Chemistry, Organic
Química orgánica
A cascade reaction of indoles with propargylic diols
involving an unprecedented metal-free 1,2-indole migration onto an
alkyne is here described. DFT calculations support a mechanism
consisting in a concerted nucleophilic attack of the indole nucleus
with loss of water followed by the 1,2-migration and subsequent
Nazarov cyclization. This Brønsted acid-catalyzed protocol affords
indole-functionalized benzofulvene derivatives in high yields.
Junta de Castilla y León(BU237U13) and Ministerio de Economía y Competitividad (MINECO) and FEDER (CTQ2013-48937-C2-1P and 2-P)
2016-11-22T09:15:54Z
2016-11-22T09:15:54Z
2015-09
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
0947-6539
http://hdl.handle.net/10259/4278
eng
Chemistry-a european journal. 2015, V. 21, n. 37, p. 12889–12893
http://dx.doi.org/10.1002/chem.201502174
info:eu-repo/semantics/openAccess
application/pdf
Wiley-VCH Verlag
https://riubu.ubu.es/bitstream/10259/4278/4/%c3%81lvarez-CEJ_2015.pdf.jpg
Hispana
TEXT
http://rightsstatements.org/vocab/CNE/1.0/
RIUBU. Repositorio Institucional de la Universidad de Burgos
http://hdl.handle.net/10259/4278