Journal
MOLECULES
Volume 24, Issue 8, Pages -Publisher
MDPI
DOI: 10.3390/molecules24081569
Keywords
beta-fluorovinyl sulfone; regioselectivity; organofluorine chemistry; copper catalysis; alkynyl sulfones; hydrogenation
Funding
- Spanish Ministerio de Economia y Competitividad [CTQ-2013-43310-P, CTQ2017-84249-P]
- Generalitat Valenciana [GV/PrometeoII/2014/073]
- Spanish Ministerio de Educacion, Cultura y Deporte [FPU15/01485]
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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)--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.
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