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Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines

We report herein studies on copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines. Treatment of N–H ketimines having an α-sp(3) hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C–C bond cleavage to give the corresponding carbonit...

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Autores principales: Tnay, Ya Lin, Ang, Gim Yean, Chiba, Shunsuke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661020/
https://www.ncbi.nlm.nih.gov/pubmed/26664613
http://dx.doi.org/10.3762/bjoc.11.209
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author Tnay, Ya Lin
Ang, Gim Yean
Chiba, Shunsuke
author_facet Tnay, Ya Lin
Ang, Gim Yean
Chiba, Shunsuke
author_sort Tnay, Ya Lin
collection PubMed
description We report herein studies on copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines. Treatment of N–H ketimines having an α-sp(3) hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C–C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalonitrile as a CN source.
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spelling pubmed-46610202015-12-09 Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines Tnay, Ya Lin Ang, Gim Yean Chiba, Shunsuke Beilstein J Org Chem Full Research Paper We report herein studies on copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines. Treatment of N–H ketimines having an α-sp(3) hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C–C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalonitrile as a CN source. Beilstein-Institut 2015-10-19 /pmc/articles/PMC4661020/ /pubmed/26664613 http://dx.doi.org/10.3762/bjoc.11.209 Text en Copyright © 2015, Tnay et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tnay, Ya Lin
Ang, Gim Yean
Chiba, Shunsuke
Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
title Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
title_full Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
title_fullStr Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
title_full_unstemmed Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
title_short Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
title_sort copper-catalyzed aerobic radical c–c bond cleavage of n–h ketimines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661020/
https://www.ncbi.nlm.nih.gov/pubmed/26664613
http://dx.doi.org/10.3762/bjoc.11.209
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