Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts

[Image: see text] The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions with N-nucleophiles of varying basicity is presented. A careful choice of the reaction conditions minimized undesired rearrangements and arylation processes, typical side reactions with Brønsted ac...

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Autores principales: Radtanajiravong, Lalita, Díez-González, Silvia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6682045/
https://www.ncbi.nlm.nih.gov/pubmed/31460347
http://dx.doi.org/10.1021/acsomega.9b01427
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author Radtanajiravong, Lalita
Díez-González, Silvia
author_facet Radtanajiravong, Lalita
Díez-González, Silvia
author_sort Radtanajiravong, Lalita
collection PubMed
description [Image: see text] The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions with N-nucleophiles of varying basicity is presented. A careful choice of the reaction conditions minimized undesired rearrangements and arylation processes, typical side reactions with Brønsted acid catalysis. These systems are compatible with technical solvents and presence of air, and they are also applicable to C-, O-, and S-nucleophiles.
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spelling pubmed-66820452019-08-27 Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts Radtanajiravong, Lalita Díez-González, Silvia ACS Omega [Image: see text] The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions with N-nucleophiles of varying basicity is presented. A careful choice of the reaction conditions minimized undesired rearrangements and arylation processes, typical side reactions with Brønsted acid catalysis. These systems are compatible with technical solvents and presence of air, and they are also applicable to C-, O-, and S-nucleophiles. American Chemical Society 2019-07-18 /pmc/articles/PMC6682045/ /pubmed/31460347 http://dx.doi.org/10.1021/acsomega.9b01427 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Radtanajiravong, Lalita
Díez-González, Silvia
Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts
title Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts
title_full Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts
title_fullStr Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts
title_full_unstemmed Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts
title_short Taming Brønsted Acid Reactivity: Nucleophilic Substitutions of Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-Based Brønsted Acid Catalysts
title_sort taming brønsted acid reactivity: nucleophilic substitutions of propargylic alcohols with n-nucleophiles mediated by phosphorus-based brønsted acid catalysts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6682045/
https://www.ncbi.nlm.nih.gov/pubmed/31460347
http://dx.doi.org/10.1021/acsomega.9b01427
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AT diezgonzalezsilvia tamingbrønstedacidreactivitynucleophilicsubstitutionsofpropargylicalcoholswithnnucleophilesmediatedbyphosphorusbasedbrønstedacidcatalysts

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