2026-06-17T21:48:51Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/60932022-11-11T12:52:48Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
From Propargylic Alcohols to Substituted Thiochromenes: gem- Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
Velasco Pérez, Noelia
Suárez, Anisley
Martínez Lara, Fernando
Fernández Rodríguez, Manuel A.
Sanz Díez, Roberto
Suarez Pantiga, Samuel
Sulfides
Alcohols
Column chromatography
Cyclization
Propargyls
Química orgánica
Chemistry, Organic
This work describes the 6-endo-dig cyclization of Saryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing
intramolecular silver-catalyzed alkyne hydroarylation and Niodosuccinimide-promoted iodoarylation. Additionally, a PTSAcatalyzed thiolation reaction of propargylic alcohols was developed
to synthesize the required tertiary S-aryl propargyl ethers. The
applicability of merging these two methods is demonstrated by
synthesizing the retinoic acid receptor antagonist AGN194310.
Junta de Castilla y León
and FEDER (BU291P18 and BU049P20) and Ministerio de
Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P)
for financial support. The project leading to these results has
received funding from “la Caixa” Foundation, under Agreement
LCF/PR/PR18/51130007> (CAIXA-UBU001). N.V.,
F.M.-L., and S.S.-P. thank Junta de Castilla y León and FSE
and FEDER for predoctoral (N.V. and F.M.-L.) and
postdoctoral (S.S.-P.) contracts, respectively.
2021-11-04T10:13:47Z
2021-11-04T10:13:47Z
2021-04
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
0022-3263
http://hdl.handle.net/10259/6093
10.1021/acs.joc.1c00333
1520-6904
eng
The Journal of Organic Chemistry. 2021, V. 86, n. 10, 7078−7091
https://doi.org/10.1021/acs.joc.1c00333
info:eu-repo/grantAgreement/Junta de Castilla y León//BU291P18
info:eu-repo/grantAgreement/Junta de Castilla y León//BU049P20
info:eu-repo/grantAgreement/Fundación Bancaria Caixa d'Estalvis i Pensions de Barcelona//LCF%2FPR%2FPR18%2F51130007 (CAIXA-UBU001)
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75023-C2-1-P/ES/DESARROLLO DE NUEVAS METODOLOGIAS SINTETICAS. APLICACION A LA PREPARACION DE MOLECULAS DE INTERES Y A LA VALORIZACION DE LA LIGNINA
Atribución 4.0 Internacional
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
application/pdf
American Chemical Society
https://riubu.ubu.es/bitstream/10259/6093/4/Velasco-joc_2021.pdf.jpg
Hispana
TEXT
http://creativecommons.org/licenses/by/4.0/
RIUBU. Repositorio Institucional de la Universidad de Burgos
http://hdl.handle.net/10259/6093