Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones

Organofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic me...

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Main Authors:	Raquel Román, Pablo Barrio, Natalia Mateu, Daniel M. Sedgwick, Santos Fustero
Format:	Article
Language:	English
Published:	MDPI AG 2019-04-01
Series:	Molecules
Subjects:	β-fluorovinyl sulfone regioselectivity organofluorine chemistry copper catalysis alkynyl sulfones hydrogenation
Online Access:	https://www.mdpi.com/1420-3049/24/8/1569

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record_format	Article
spelling	doaj-f236a01c5f044879933a83145943f1652020-11-25T00:50:34ZengMDPI AGMolecules1420-30492019-04-01248156910.3390/molecules24081569molecules24081569Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl SulfonesRaquel Román0Pablo Barrio1Natalia Mateu2Daniel M. Sedgwick3Santos Fustero4Departamento de Química Orgánica, Universitat de València, 46100 Burjassot, SpainDepartamento de Química Orgánica e Inorgánica, Avda. Julián Clavería nº 8, 33006 Oviedo, SpainLaboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, SpainDepartamento de Química Orgánica, Universitat de València, 46100 Burjassot, SpainDepartamento de Química Orgánica, Universitat de València, 46100 Burjassot, SpainOrganofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic methodologies. In this article, we present the synthesis of a series of previously undescribed (<i>E</i>)-β-fluorovinyl sulfones via a simple copper-catalyzed addition of hydrogen fluoride to alkynyl sulfone starting materials in varying yields and <i>E/Z</i> selectivities. The hydrogenation of these products was also explored and compared with the hydrogenation of the related <i>Z</i> isomers. These new products may find interesting applications, given the versatility of vinyl sulfones in chemical synthesis and the unique properties of vinyl fluorides in biological settings.https://www.mdpi.com/1420-3049/24/8/1569β-fluorovinyl sulfoneregioselectivityorganofluorine chemistrycopper catalysisalkynyl sulfoneshydrogenation
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Raquel Román Pablo Barrio Natalia Mateu Daniel M. Sedgwick Santos Fustero
spellingShingle	Raquel Román Pablo Barrio Natalia Mateu Daniel M. Sedgwick Santos Fustero Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones Molecules β-fluorovinyl sulfone regioselectivity organofluorine chemistry copper catalysis alkynyl sulfones hydrogenation
author_facet	Raquel Román Pablo Barrio Natalia Mateu Daniel M. Sedgwick Santos Fustero
author_sort	Raquel Román
title	Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones
title_short	Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones
title_full	Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones
title_fullStr	Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones
title_full_unstemmed	Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones
title_sort	copper-catalyzed regioselective synthesis of (<i>e</i>)-β-fluorovinyl sulfones
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2019-04-01
description	Organofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic methodologies. In this article, we present the synthesis of a series of previously undescribed (<i>E</i>)-β-fluorovinyl sulfones via a simple copper-catalyzed addition of hydrogen fluoride to alkynyl sulfone starting materials in varying yields and <i>E/Z</i> selectivities. The hydrogenation of these products was also explored and compared with the hydrogenation of the related <i>Z</i> isomers. These new products may find interesting applications, given the versatility of vinyl sulfones in chemical synthesis and the unique properties of vinyl fluorides in biological settings.
topic	β-fluorovinyl sulfone regioselectivity organofluorine chemistry copper catalysis alkynyl sulfones hydrogenation
url	https://www.mdpi.com/1420-3049/24/8/1569
work_keys_str_mv	AT raquelroman coppercatalyzedregioselectivesynthesisofieibfluorovinylsulfones AT pablobarrio coppercatalyzedregioselectivesynthesisofieibfluorovinylsulfones AT nataliamateu coppercatalyzedregioselectivesynthesisofieibfluorovinylsulfones AT danielmsedgwick coppercatalyzedregioselectivesynthesisofieibfluorovinylsulfones AT santosfustero coppercatalyzedregioselectivesynthesisofieibfluorovinylsulfones
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Copper-Catalyzed Regioselective Synthesis of (<i>E</i>)-β-Fluorovinyl Sulfones

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