Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes

[Image: see text] We report the use of cationic gold complexes [Au(NHC)(CH(3)CN)][BF(4)] and [{Au(NHC)}(2)(μ–OH)][BF(4)] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protoco...

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Autores principales: Veenboer, Richard M. P., Dupuy, Stéphanie, Nolan, Steven P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5745073/
https://www.ncbi.nlm.nih.gov/pubmed/29291136
http://dx.doi.org/10.1021/cs501976s
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author Veenboer, Richard M. P.
Dupuy, Stéphanie
Nolan, Steven P.
author_facet Veenboer, Richard M. P.
Dupuy, Stéphanie
Nolan, Steven P.
author_sort Veenboer, Richard M. P.
collection PubMed
description [Image: see text] We report the use of cationic gold complexes [Au(NHC)(CH(3)CN)][BF(4)] and [{Au(NHC)}(2)(μ–OH)][BF(4)] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h(–1)).
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spelling pubmed-57450732017-12-28 Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes Veenboer, Richard M. P. Dupuy, Stéphanie Nolan, Steven P. ACS Catal [Image: see text] We report the use of cationic gold complexes [Au(NHC)(CH(3)CN)][BF(4)] and [{Au(NHC)}(2)(μ–OH)][BF(4)] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h(–1)). American Chemical Society 2015-01-21 2015-02-06 /pmc/articles/PMC5745073/ /pubmed/29291136 http://dx.doi.org/10.1021/cs501976s Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Veenboer, Richard M. P.
Dupuy, Stéphanie
Nolan, Steven P.
Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes
title Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes
title_full Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes
title_fullStr Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes
title_full_unstemmed Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes
title_short Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes
title_sort stereoselective gold(i)-catalyzed intermolecular hydroalkoxlation of alkynes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5745073/
https://www.ncbi.nlm.nih.gov/pubmed/29291136
http://dx.doi.org/10.1021/cs501976s
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