2026-05-28T18:05:11Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/60902022-12-02T01:05:49Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Gold-Catalyzed Reactions of 2-Alkynyl-1-indolyl-1,2-diols with Thiols: Stereoselective Synthesis of (Z)-α-Indol-3-yl α-(2-Thioalkenyl) Ketones
Martínez Lara, Fernando
Suárez, Anisley
Velasco Pérez, Noelia
Suarez Pantiga, Samuel
Sanz Díez, Roberto
Gold
Homogeneous catalysis
Nitrogen heterocycles
Rearrangement
Sulfur
Química orgánica
Chemistry, Organic
Propargylic glycols, 2-alkynyl-1-(indol-3-yl)-1,2-diols, react with thiols undergoing a complex but
selective gold-catalyzed transformation that gives rise to α-indol-3-yl α-((Z)-2-thioalkenyl) ketones. The
sequence is triggered by the regioselective thiolation of indolyl diols followed by an attack of the sulfur instead
of the indole over the activated alkyne. The final compounds are obtained in remarkably high yields and arise
from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide and thiols.
Ministerio de Ciencia e Innovación
and FEDER (CTQ2016-75023-C2-1-P and PID2020-
115789GB-C21), and Junta de Castilla y León and FEDER
(BU291P18 and BU049P20) for financial support. The project
leading to these results has received funding from “la Caixa”
Foundation, under the Agreement LCF/PR/PR18/51130007>
(CAIXA-UBU001). F. M.-L., N. V. and S. S.-P. thank Junta de
Castilla y León (Consejería de Educación) and Fondo Social
Europeo for predoctoral (F. M.-L. and N. V) and postdoctoral
(S. S.-P.) contracts, respectively.
2021-11-04T09:29:09Z
2021-11-04T09:29:09Z
2022-01
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
1615-4169
http://hdl.handle.net/10259/6090
10.1002/adsc.202100930
eng
Advanced Synthesis & Catalysis. 2022, V. 364, n. 1, p. 132-138
https://doi.org/10.1002/adsc.202100930
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
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-115789GB-C21/ES/ESTRATEGIAS SINTETICAS SOSTENIBLES PARA LA TRANSFORMACION DIRECTA DE NITROCOMPUESTOS Y DESARROLLO DE NUEVAS REACCIONES CATALIZADAS POR ORO
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)
Atribución-NoComercial 4.0 Internacional
http://creativecommons.org/licenses/by-nc/4.0/
info:eu-repo/semantics/openAccess
application/pdf
Wiley