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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...

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Autores principales: Guan, Zhipeng, Zhu, Shuxiang, Yang, Yankai, Liu, Yanlong, Wang, Siyuan, Bu, Faxiang, Cong, Hengjiang, Alhumade, Hesham, Zhang, Heng, Lei, Aiwen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
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.
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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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