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Open AccessFeature PaperArticle

Copper-Catalyzed Regioselective Synthesis of (E)-β-Fluorovinyl Sulfones

1
Departamento de Química Orgánica, Universitat de València, 46100 Burjassot, Spain
2
Departamento de Química Orgánica e Inorgánica, Avda. Julián Clavería nº 8, 33006 Oviedo, Spain
3
Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(8), 1569; https://doi.org/10.3390/molecules24081569
Received: 4 April 2019 / Revised: 17 April 2019 / Accepted: 19 April 2019 / Published: 20 April 2019
(This article belongs to the Special Issue Fabulous Fluorine in Organic and Medicinal Chemistry)
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 (E)-β-fluorovinyl sulfones via a simple copper-catalyzed addition of hydrogen fluoride to alkynyl sulfone starting materials in varying yields and E/Z selectivities. The hydrogenation of these products was also explored and compared with the hydrogenation of the related Z 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. View Full-Text
Keywords: β-fluorovinyl sulfone; regioselectivity; organofluorine chemistry; copper catalysis; alkynyl sulfones; hydrogenation β-fluorovinyl sulfone; regioselectivity; organofluorine chemistry; copper catalysis; alkynyl sulfones; hydrogenation
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MDPI and ACS Style

Román, R.; Barrio, P.; Mateu, N.; Sedgwick, D.M.; Fustero, S. Copper-Catalyzed Regioselective Synthesis of (E)-β-Fluorovinyl Sulfones. Molecules 2019, 24, 1569.

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