Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone

A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones via an unprecedented “cyano-borrowing reaction” has been developed. Cleavage of the C–CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to α,β-unsaturat...

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Detalles Bibliográficos
Autores principales: Li, Zhao-Feng, Li, Qian, Ren, Li-Qing, Li, Qing-Hua, Peng, Yun-Gui, Liu, Tang-Lin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6568282/
https://www.ncbi.nlm.nih.gov/pubmed/31293766
http://dx.doi.org/10.1039/c9sc00640k
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author Li, Zhao-Feng
Li, Qian
Ren, Li-Qing
Li, Qing-Hua
Peng, Yun-Gui
Liu, Tang-Lin
author_facet Li, Zhao-Feng
Li, Qian
Ren, Li-Qing
Li, Qing-Hua
Peng, Yun-Gui
Liu, Tang-Lin
author_sort Li, Zhao-Feng
collection PubMed
description A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones via an unprecedented “cyano-borrowing reaction” has been developed. Cleavage of the C–CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to α,β-unsaturated ketones proceeded to deliver a range of racemic β-cyano ketones with good to high yields. The practical procedure with the use of a commercial and less-toxic CN source bodes well for wide application of this protocol.
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spelling pubmed-65682822019-07-10 Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone Li, Zhao-Feng Li, Qian Ren, Li-Qing Li, Qing-Hua Peng, Yun-Gui Liu, Tang-Lin Chem Sci Chemistry A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones via an unprecedented “cyano-borrowing reaction” has been developed. Cleavage of the C–CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to α,β-unsaturated ketones proceeded to deliver a range of racemic β-cyano ketones with good to high yields. The practical procedure with the use of a commercial and less-toxic CN source bodes well for wide application of this protocol. Royal Society of Chemistry 2019-05-06 /pmc/articles/PMC6568282/ /pubmed/31293766 http://dx.doi.org/10.1039/c9sc00640k Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Li, Zhao-Feng
Li, Qian
Ren, Li-Qing
Li, Qing-Hua
Peng, Yun-Gui
Liu, Tang-Lin
Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
title Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
title_full Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
title_fullStr Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
title_full_unstemmed Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
title_short Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
title_sort cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6568282/
https://www.ncbi.nlm.nih.gov/pubmed/31293766
http://dx.doi.org/10.1039/c9sc00640k
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