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Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides
The construction of C(sp(2))–X (X = B, N, O, Si, P, S, Se, etc.) bonds has drawn growing attention since heteroatomic compounds play a prominent role from biological to pharmaceutical sciences. The current study demonstrates the C(sp(2))–S/Se and C(sp(2))–N bond formation of one carbon of isocyanide...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8565391/ https://www.ncbi.nlm.nih.gov/pubmed/34760196 http://dx.doi.org/10.1039/d1sc04475c |
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author | Guan, Zhipeng Zhu, Shuxiang Yang, Yankai Liu, Yanlong Wang, Siyuan Bu, Faxiang Cong, Hengjiang Alhumade, Hesham Zhang, Heng Lei, Aiwen |
author_facet | Guan, Zhipeng Zhu, Shuxiang Yang, Yankai Liu, Yanlong Wang, Siyuan Bu, Faxiang Cong, Hengjiang Alhumade, Hesham Zhang, Heng Lei, Aiwen |
author_sort | Guan, Zhipeng |
collection | PubMed |
description | The construction of C(sp(2))–X (X = B, N, O, Si, P, S, Se, etc.) bonds has drawn growing attention since heteroatomic compounds play a prominent role from biological to pharmaceutical sciences. The current study demonstrates the C(sp(2))–S/Se and C(sp(2))–N bond formation of one carbon of isocyanides with thiophenols or disulfides or diselenides and azazoles simultaneously. The reported findings could provide access to novel multiple isothioureas, especially hitherto rarely reported selenoureas. The protocol showed good atom-economy and step-economy with only hydrogen evolution and theoretical calculations accounted for the stereoselectivity of the products. Importantly, the electrochemical reaction could exclusively occur at the isocyano part regardless of the presence of susceptible radical acceptors, such as a broad range of arenes and alkynyl moieties, even alkenyl moieties. |
format | Online Article Text |
id | pubmed-8565391 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-85653912021-11-09 Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides Guan, Zhipeng Zhu, Shuxiang Yang, Yankai Liu, Yanlong Wang, Siyuan Bu, Faxiang Cong, Hengjiang Alhumade, Hesham Zhang, Heng Lei, Aiwen Chem Sci Chemistry The construction of C(sp(2))–X (X = B, N, O, Si, P, S, Se, etc.) bonds has drawn growing attention since heteroatomic compounds play a prominent role from biological to pharmaceutical sciences. The current study demonstrates the C(sp(2))–S/Se and C(sp(2))–N bond formation of one carbon of isocyanides with thiophenols or disulfides or diselenides and azazoles simultaneously. The reported findings could provide access to novel multiple isothioureas, especially hitherto rarely reported selenoureas. The protocol showed good atom-economy and step-economy with only hydrogen evolution and theoretical calculations accounted for the stereoselectivity of the products. Importantly, the electrochemical reaction could exclusively occur at the isocyano part regardless of the presence of susceptible radical acceptors, such as a broad range of arenes and alkynyl moieties, even alkenyl moieties. The Royal Society of Chemistry 2021-10-01 /pmc/articles/PMC8565391/ /pubmed/34760196 http://dx.doi.org/10.1039/d1sc04475c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Guan, Zhipeng Zhu, Shuxiang Yang, Yankai Liu, Yanlong Wang, Siyuan Bu, Faxiang Cong, Hengjiang Alhumade, Hesham Zhang, Heng Lei, Aiwen Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides |
title | Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides |
title_full | Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides |
title_fullStr | Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides |
title_full_unstemmed | Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides |
title_short | Electrochemically selective double C(sp(2))–X (X = S/Se, N) bond formation of isocyanides |
title_sort | electrochemically selective double c(sp(2))–x (x = s/se, n) bond formation of isocyanides |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8565391/ https://www.ncbi.nlm.nih.gov/pubmed/34760196 http://dx.doi.org/10.1039/d1sc04475c |
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