Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides

[Image: see text] A new simple method for the synthesis of 2-ethynylphenyl(diaryl)phosphine oxides via ring opening of benzophosphol-3-yl triflates has been developed. This process occurs via nucleophilic attack of a Grignard reagent at the phosphorus center, which results in ring opening and cleava...

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Autores principales: Ponikiewski, Łukasz, Sowa, Sylwia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576819/
https://www.ncbi.nlm.nih.gov/pubmed/34699223
http://dx.doi.org/10.1021/acs.joc.1c01629
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author Ponikiewski, Łukasz
Sowa, Sylwia
author_facet Ponikiewski, Łukasz
Sowa, Sylwia
author_sort Ponikiewski, Łukasz
collection PubMed
description [Image: see text] A new simple method for the synthesis of 2-ethynylphenyl(diaryl)phosphine oxides via ring opening of benzophosphol-3-yl triflates has been developed. This process occurs via nucleophilic attack of a Grignard reagent at the phosphorus center, which results in ring opening and cleavage of a leaving group. The reaction proceeds under mild conditions and, within 15–60 min, leads to a library of previously unavailable 2-ethynylphenylphosphine oxides in yields up to 98%.
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spelling pubmed-85768192021-11-10 Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides Ponikiewski, Łukasz Sowa, Sylwia J Org Chem [Image: see text] A new simple method for the synthesis of 2-ethynylphenyl(diaryl)phosphine oxides via ring opening of benzophosphol-3-yl triflates has been developed. This process occurs via nucleophilic attack of a Grignard reagent at the phosphorus center, which results in ring opening and cleavage of a leaving group. The reaction proceeds under mild conditions and, within 15–60 min, leads to a library of previously unavailable 2-ethynylphenylphosphine oxides in yields up to 98%. American Chemical Society 2021-10-26 2021-11-05 /pmc/articles/PMC8576819/ /pubmed/34699223 http://dx.doi.org/10.1021/acs.joc.1c01629 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ponikiewski, Łukasz
Sowa, Sylwia
Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides
title Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides
title_full Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides
title_fullStr Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides
title_full_unstemmed Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides
title_short Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides
title_sort ring opening of triflates derived from benzophospholan-3-one oxides by aryl grignard reagents as a route to 2-ethynylphenyl(diaryl)phosphine oxides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576819/
https://www.ncbi.nlm.nih.gov/pubmed/34699223
http://dx.doi.org/10.1021/acs.joc.1c01629
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AT sowasylwia ringopeningoftriflatesderivedfrombenzophospholan3oneoxidesbyarylgrignardreagentsasarouteto2ethynylphenyldiarylphosphineoxides

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