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Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds

The 1,4-addition of a monofluoromethyl nucleophile to a variety of α,β-unsaturated compounds has been achieved under mild conditions using either phosphines or potassium carbonate at room temperature. α-Substituted fluoro(phenylsulfonyl)methane easily undergoes Michael addition to α,β-unsaturated ke...

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Detalles Bibliográficos
Autores principales: Prakash, G K Surya, Zhao, Xiaoming, Chacko, Sujith, Wang, Fang, Vaghoo, Habiba, Olah, George A
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486456/
https://www.ncbi.nlm.nih.gov/pubmed/18941481
http://dx.doi.org/10.3762/bjoc.4.17
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author Prakash, G K Surya
Zhao, Xiaoming
Chacko, Sujith
Wang, Fang
Vaghoo, Habiba
Olah, George A
author_facet Prakash, G K Surya
Zhao, Xiaoming
Chacko, Sujith
Wang, Fang
Vaghoo, Habiba
Olah, George A
author_sort Prakash, G K Surya
collection PubMed
description The 1,4-addition of a monofluoromethyl nucleophile to a variety of α,β-unsaturated compounds has been achieved under mild conditions using either phosphines or potassium carbonate at room temperature. α-Substituted fluoro(phenylsulfonyl)methane easily undergoes Michael addition to α,β-unsaturated ketones, esters, nitriles, sulfones, as well as propynoates at room temperature to yield the corresponding adducts in moderate to excellent yields.
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spelling pubmed-24864562008-10-20 Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds Prakash, G K Surya Zhao, Xiaoming Chacko, Sujith Wang, Fang Vaghoo, Habiba Olah, George A Beilstein J Org Chem Full Research Paper The 1,4-addition of a monofluoromethyl nucleophile to a variety of α,β-unsaturated compounds has been achieved under mild conditions using either phosphines or potassium carbonate at room temperature. α-Substituted fluoro(phenylsulfonyl)methane easily undergoes Michael addition to α,β-unsaturated ketones, esters, nitriles, sulfones, as well as propynoates at room temperature to yield the corresponding adducts in moderate to excellent yields. Beilstein-Institut 2008-05-21 /pmc/articles/PMC2486456/ /pubmed/18941481 http://dx.doi.org/10.3762/bjoc.4.17 Text en Copyright © 2008, Prakash 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
Prakash, G K Surya
Zhao, Xiaoming
Chacko, Sujith
Wang, Fang
Vaghoo, Habiba
Olah, George A
Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds
title Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds
title_full Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds
title_fullStr Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds
title_full_unstemmed Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds
title_short Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds
title_sort efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486456/
https://www.ncbi.nlm.nih.gov/pubmed/18941481
http://dx.doi.org/10.3762/bjoc.4.17
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