A Titanium‐Catalyzed Reductive α‐Desulfonylation

A titanium(III)‐catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α‐sulfonyl nitriles, circumventing traditional base‐mediated α‐alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohol...

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Detalles Bibliográficos
Autores principales: Kern, Christoph, Selau, Jan, Streuff, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048938/
https://www.ncbi.nlm.nih.gov/pubmed/33539578
http://dx.doi.org/10.1002/chem.202005400
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author Kern, Christoph
Selau, Jan
Streuff, Jan
author_facet Kern, Christoph
Selau, Jan
Streuff, Jan
author_sort Kern, Christoph
collection PubMed
description A titanium(III)‐catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α‐sulfonyl nitriles, circumventing traditional base‐mediated α‐alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α‐desulfonylation of ketones. In addition, a one‐pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst‐dependent mechanism involving a homolytic C−S cleavage.
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spelling pubmed-80489382021-04-20 A Titanium‐Catalyzed Reductive α‐Desulfonylation Kern, Christoph Selau, Jan Streuff, Jan Chemistry Communications A titanium(III)‐catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α‐sulfonyl nitriles, circumventing traditional base‐mediated α‐alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α‐desulfonylation of ketones. In addition, a one‐pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst‐dependent mechanism involving a homolytic C−S cleavage. John Wiley and Sons Inc. 2021-03-05 2021-04-07 /pmc/articles/PMC8048938/ /pubmed/33539578 http://dx.doi.org/10.1002/chem.202005400 Text en © 2021 The Authors. Published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Kern, Christoph
Selau, Jan
Streuff, Jan
A Titanium‐Catalyzed Reductive α‐Desulfonylation
title A Titanium‐Catalyzed Reductive α‐Desulfonylation
title_full A Titanium‐Catalyzed Reductive α‐Desulfonylation
title_fullStr A Titanium‐Catalyzed Reductive α‐Desulfonylation
title_full_unstemmed A Titanium‐Catalyzed Reductive α‐Desulfonylation
title_short A Titanium‐Catalyzed Reductive α‐Desulfonylation
title_sort titanium‐catalyzed reductive α‐desulfonylation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048938/
https://www.ncbi.nlm.nih.gov/pubmed/33539578
http://dx.doi.org/10.1002/chem.202005400
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AT selaujan atitaniumcatalyzedreductiveadesulfonylation
AT streuffjan atitaniumcatalyzedreductiveadesulfonylation
AT kernchristoph titaniumcatalyzedreductiveadesulfonylation
AT selaujan titaniumcatalyzedreductiveadesulfonylation
AT streuffjan titaniumcatalyzedreductiveadesulfonylation

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