A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates

An efficient and catalyst-free synthesis of trisubstituted allylic sulfones through an allylic sulfonylation reaction of Morita-Baylis-Hillman (MBH) carbonates with sodium sulfinates has been developed. Under the optimized reaction conditions, a series of trisubstituted allylic sulfones were rapidly...

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Autores principales: Jiang, Lin, Li, Yong-Gen, Zhou, Jiang-Feng, Chuan, Yong-Ming, Li, Hong-Li, Yuan, Ming-Long
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272667/
https://www.ncbi.nlm.nih.gov/pubmed/25961162
http://dx.doi.org/10.3390/molecules20058213
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author Jiang, Lin
Li, Yong-Gen
Zhou, Jiang-Feng
Chuan, Yong-Ming
Li, Hong-Li
Yuan, Ming-Long
author_facet Jiang, Lin
Li, Yong-Gen
Zhou, Jiang-Feng
Chuan, Yong-Ming
Li, Hong-Li
Yuan, Ming-Long
author_sort Jiang, Lin
collection PubMed
description An efficient and catalyst-free synthesis of trisubstituted allylic sulfones through an allylic sulfonylation reaction of Morita-Baylis-Hillman (MBH) carbonates with sodium sulfinates has been developed. Under the optimized reaction conditions, a series of trisubstituted allylic sulfones were rapidly prepared in good to excellent yields (71%–99%) with good to high selectivity (Z/E from 79:21 to >99:1). Compared with known synthetic methods, the current protocol features mild reaction temperature, high efficiency and easily available reagents.
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spelling pubmed-62726672019-01-07 A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates Jiang, Lin Li, Yong-Gen Zhou, Jiang-Feng Chuan, Yong-Ming Li, Hong-Li Yuan, Ming-Long Molecules Article An efficient and catalyst-free synthesis of trisubstituted allylic sulfones through an allylic sulfonylation reaction of Morita-Baylis-Hillman (MBH) carbonates with sodium sulfinates has been developed. Under the optimized reaction conditions, a series of trisubstituted allylic sulfones were rapidly prepared in good to excellent yields (71%–99%) with good to high selectivity (Z/E from 79:21 to >99:1). Compared with known synthetic methods, the current protocol features mild reaction temperature, high efficiency and easily available reagents. MDPI 2015-05-07 /pmc/articles/PMC6272667/ /pubmed/25961162 http://dx.doi.org/10.3390/molecules20058213 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Jiang, Lin
Li, Yong-Gen
Zhou, Jiang-Feng
Chuan, Yong-Ming
Li, Hong-Li
Yuan, Ming-Long
A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
title A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
title_full A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
title_fullStr A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
title_full_unstemmed A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
title_short A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
title_sort facile and mild synthesis of trisubstituted allylic sulfones from morita-baylis-hillman carbonates
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272667/
https://www.ncbi.nlm.nih.gov/pubmed/25961162
http://dx.doi.org/10.3390/molecules20058213
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