Julia Olefination as a General Route to Phenyl (α-Fluoro)vinyl Sulfones

Abstract

Mild and efficient synthesis of phenyl (alpha-fluoro)vinyl sulfones via condensation of aldehydes and a ketone with a novel benzothiazolyl based bis-sulfone reagent is reported and this proceeds with moderate to good Z-stereoselectivity.

Visible-light-driven graphitic carbon nitride-catalyzed ATRA of alkynes: highly regio- and stereoselective synthesis of (E)-β-functionalized vinylsulfones

“…Vinylsulfones are ubiquitous in pharmaceuticals and bioactive molecules, 13 and are also important organic building blocks 14 (Scheme 2a). The conventional approaches for the synthesis of vinylsulfones involve addition, oxidation, and elimination reactions 15 (Scheme 2b), which require tedious operations and complex purification processes, and also suffer from poor atom economy. Atom transfer radical addition (ATRA) of alkynes is a straightforward and atom economical way to construct various functionalized vinylsulfones.…”

Synthesis of Regiospecifically Fluorinated Conjugated Dienamides

“…Fluorine is an attractive substituent in pharmaceuticals, in agrochemicals, and in materials chemistry [ 14 , 15 , 16 ] due to its effect on physical, chemical, and biological properties of compounds [ 17 , 18 , 19 ]. Julia-Kocienski olefinations [ 20 , 21 , 22 , 23 ] have been explored for the synthesis of various functionalized fluoroolefins [ 24 , 25 , 26 ] by us [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ] and by others [ 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 ]. In the course of our recent work, we became interested in the use of bifunctional Julia-Kocienski reagents, or their precursors, for novel modular assembly of vinyl [ 33 , 47 ] and fluorovinyl [ 33 ] compounds.…”