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Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds
A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective α-sulfenylation/β-thiolation of α,β-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at α- or β-position of carbonyls with different sulfur reage...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070314/ https://www.ncbi.nlm.nih.gov/pubmed/35531013 http://dx.doi.org/10.1039/c9ra05708k |
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author | Huang, Xi Li, Juan Li, Xiang Wang, Jiayi Peng, Yanqing Song, Gonghua |
author_facet | Huang, Xi Li, Juan Li, Xiang Wang, Jiayi Peng, Yanqing Song, Gonghua |
author_sort | Huang, Xi |
collection | PubMed |
description | A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective α-sulfenylation/β-thiolation of α,β-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at α- or β-position of carbonyls with different sulfur reagents under slightly changed reaction conditions. A series of desired products were obtained in moderate to excellent yields. Mechanistic studies revealed that B(2)pin(2) played the key role in activating the transformation towards the β-thiolation of α,β-unsaturated carbonyl compounds. This transition-metal-catalyst-free method provides a convenient and efficient tool for the highly chemoselective preparation of α-thiolation or β-sulfenylation products of α,β-unsaturated carbonyl compounds. |
format | Online Article Text |
id | pubmed-9070314 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90703142022-05-05 Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds Huang, Xi Li, Juan Li, Xiang Wang, Jiayi Peng, Yanqing Song, Gonghua RSC Adv Chemistry A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective α-sulfenylation/β-thiolation of α,β-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at α- or β-position of carbonyls with different sulfur reagents under slightly changed reaction conditions. A series of desired products were obtained in moderate to excellent yields. Mechanistic studies revealed that B(2)pin(2) played the key role in activating the transformation towards the β-thiolation of α,β-unsaturated carbonyl compounds. This transition-metal-catalyst-free method provides a convenient and efficient tool for the highly chemoselective preparation of α-thiolation or β-sulfenylation products of α,β-unsaturated carbonyl compounds. The Royal Society of Chemistry 2019-08-22 /pmc/articles/PMC9070314/ /pubmed/35531013 http://dx.doi.org/10.1039/c9ra05708k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Huang, Xi Li, Juan Li, Xiang Wang, Jiayi Peng, Yanqing Song, Gonghua Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds |
title | Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds |
title_full | Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds |
title_fullStr | Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds |
title_full_unstemmed | Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds |
title_short | Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds |
title_sort | catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070314/ https://www.ncbi.nlm.nih.gov/pubmed/35531013 http://dx.doi.org/10.1039/c9ra05708k |
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