Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles

Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/P-nucleophiles (phosphine chalcogenides,...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Boris A. Trofimov, Pavel A. Volkov, Anton A. Telezhkin
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	electron-deficient acetylenes PH–nucleophiles pyridines quinolines isoquinolines acridine Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/8dadd64bf56a46039b2a1f486fa621ae
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:8dadd64bf56a46039b2a1f486fa621ae
record_format	dspace
spelling	oai:doaj.org-article:8dadd64bf56a46039b2a1f486fa621ae2021-11-25T18:27:31ZElectron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles10.3390/molecules262268241420-3049https://doaj.org/article/8dadd64bf56a46039b2a1f486fa621ae2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6824https://doaj.org/toc/1420-3049Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/<i>P</i>-nucleophiles (phosphine chalcogenides, <i>H</i>-phosphonates) are reviewed. Special attention is focused on a S<sub>N</sub><sup>H</sup> reaction of the regioselective cross-coupling of pyridines with secondary phosphine chalcogenides triggered by acylacetylenes to give 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as three-modal adjuvants (i) activating the pyridine ring towards <i>P</i>-nucleophiles, (ii) deprotonating the P-H bond and (iii) facilitating the nucleophilic addition of the <i>P</i>-centered anion to a heterocyclic moiety followed by the release of the selectively reduced acetylenes (<i>E</i>-alkenes).Boris A. TrofimovPavel A. VolkovAnton A. TelezhkinMDPI AGarticleelectron-deficient acetylenesPH–nucleophilespyridinesquinolinesisoquinolinesacridineOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6824, p 6824 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	electron-deficient acetylenes PH–nucleophiles pyridines quinolines isoquinolines acridine Organic chemistry QD241-441
spellingShingle	electron-deficient acetylenes PH–nucleophiles pyridines quinolines isoquinolines acridine Organic chemistry QD241-441 Boris A. Trofimov Pavel A. Volkov Anton A. Telezhkin Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles
description	Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/<i>P</i>-nucleophiles (phosphine chalcogenides, <i>H</i>-phosphonates) are reviewed. Special attention is focused on a S<sub>N</sub><sup>H</sup> reaction of the regioselective cross-coupling of pyridines with secondary phosphine chalcogenides triggered by acylacetylenes to give 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as three-modal adjuvants (i) activating the pyridine ring towards <i>P</i>-nucleophiles, (ii) deprotonating the P-H bond and (iii) facilitating the nucleophilic addition of the <i>P</i>-centered anion to a heterocyclic moiety followed by the release of the selectively reduced acetylenes (<i>E</i>-alkenes).
format	article
author	Boris A. Trofimov Pavel A. Volkov Anton A. Telezhkin
author_facet	Boris A. Trofimov Pavel A. Volkov Anton A. Telezhkin
author_sort	Boris A. Trofimov
title	Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles
title_short	Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles
title_full	Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles
title_fullStr	Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles
title_full_unstemmed	Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles
title_sort	electron-deficient acetylenes as three-modal adjuvants in s<sub>n</sub><sup>h</sup> reaction of pyridinoids with phosphorus nucleophiles
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/8dadd64bf56a46039b2a1f486fa621ae
work_keys_str_mv	AT borisatrofimov electrondeficientacetylenesasthreemodaladjuvantsinssubnsubsuphsupreactionofpyridinoidswithphosphorusnucleophiles AT pavelavolkov electrondeficientacetylenesasthreemodaladjuvantsinssubnsubsuphsupreactionofpyridinoidswithphosphorusnucleophiles AT antonatelezhkin electrondeficientacetylenesasthreemodaladjuvantsinssubnsubsuphsupreactionofpyridinoidswithphosphorusnucleophiles
_version_	1718411143914979328

Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles

Ejemplares similares