A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles

A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru‐catalyzed selective C−H‐oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using...

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Autores principales: Eisele, Pascal, Bauder, Michael, Hsu, Shih‐Fan, Plietker, Bernd
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6547944/
https://www.ncbi.nlm.nih.gov/pubmed/31172005
http://dx.doi.org/10.1002/open.201900130
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author Eisele, Pascal
Bauder, Michael
Hsu, Shih‐Fan
Plietker, Bernd
author_facet Eisele, Pascal
Bauder, Michael
Hsu, Shih‐Fan
Plietker, Bernd
author_sort Eisele, Pascal
collection PubMed
description A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru‐catalyzed selective C−H‐oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using silanes. The obtained acylcyanides can be employed in a plethora of transformation as exemplified to some larger extend in the sequence of C−H‐oxidation‐Tischenko‐rearrangement for the generation of structurally diverse benzoyloxycyanohydrines.
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spelling pubmed-65479442019-06-06 A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles Eisele, Pascal Bauder, Michael Hsu, Shih‐Fan Plietker, Bernd ChemistryOpen Communications A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru‐catalyzed selective C−H‐oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using silanes. The obtained acylcyanides can be employed in a plethora of transformation as exemplified to some larger extend in the sequence of C−H‐oxidation‐Tischenko‐rearrangement for the generation of structurally diverse benzoyloxycyanohydrines. John Wiley and Sons Inc. 2019-04-25 /pmc/articles/PMC6547944/ /pubmed/31172005 http://dx.doi.org/10.1002/open.201900130 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Eisele, Pascal
Bauder, Michael
Hsu, Shih‐Fan
Plietker, Bernd
A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles
title A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles
title_full A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles
title_fullStr A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles
title_full_unstemmed A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles
title_short A Cyanide‐Free Synthesis of Acylcyanides through Ru‐Catalyzed C(sp(3))‐H‐Oxidation of Benzylic Nitriles
title_sort cyanide‐free synthesis of acylcyanides through ru‐catalyzed c(sp(3))‐h‐oxidation of benzylic nitriles
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6547944/
https://www.ncbi.nlm.nih.gov/pubmed/31172005
http://dx.doi.org/10.1002/open.201900130
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