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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Beilstein-Institut
2015
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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. |
format | Online Article Text |
id | pubmed-4661020 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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