174075-36-6Relevant academic research and scientific papers
Julia olefination as a general route to phenyl (α-fluoro)vinyl sulfones
He, Maggie,Ghosh, Arun K.,Zajc, Barbara
body text, p. 999 - 1004 (2009/04/04)
Mild and efficient synthesis of phenyl (α-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. Georg Thieme Verlag Stuttgart.
Radical-mediated silyl- and germyldesulfonylation of vinyl and (α-fluoro)vinyl sulfones: Application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings
Wnuk, Stanislaw F.,Garcia Jr., Pedro I.,Wang, Zhizhong
, p. 2047 - 2049 (2007/10/03)
Equation presented. Radical-mediated silyl- and germyldesulfonylations of various vinyl and (α-fluoro)vinyl sulfones with tris(trimethylsilyl)silane and germanium hydrides provide access to vinyl and (α-fluoro)vinyl silanes and germanes. Upon oxidative treatment with hydrogen peroxide in basic aqueous solution, the vinyl tris(trimethylsilyl)silanes and -germanes undergo Pd-catalyzed cross-couplings with aryl halides.
A new synthesis of α-fluorovinylsulfones utilizing the Peterson olefination methodology
Asakura, Noriaki,Usuki, Yoshinosuke,Iio, Hideo
, p. 81 - 88 (2007/10/03)
α-Fluoro-α-silyl-substituted sulfones 1 are readily prepared from fluoromethyl phenyl sulfone and the appropriate silyl chloride. The use of TBSCl improves both the stability and yield of 1. Lithium derivatives 4 undergo a smooth Peterson olefination reaction with less-enolizable carbonyl compounds to give moderate to good yields of the expected α-fluorovinylsulfones 6, in some cases with high E-stereoselectivity. One-pot reaction with 4 generated in situ from fluoromethyl phenyl sulfone in tetrahydrofuran (THF) also proceeds smoothly, particularly with aldehydes.
Stereospecific synthesis of 1-fluoro olefins via (fluoro-vinyl)stannanes and an unequivocal NMR method for the assignment of fluoro olefin geometry
McCarthy,Huber,Le,Laskovics,Matthews
, p. 45 - 58 (2007/10/02)
(E)- and (Z)-Fluorovinyl sulfones (II) form (fluorovinyl)stannanes (III) on treatment with two equivalents of tributyltin hydride and a catalytic amount of AIBN; the free radical catalyzed reaction proceeds with retention of configuration for 2,2-disubstituted fluorovinyl sulfones (IIa and IIb). Conversion of III to 1-fluoro olefins (IV) is a stereospecific reaction and provides a general method to (E) and (Z) fluoro olefins. The utility of this method is exemplified by the synthesis of the deutero fluoro olefins 27, nucleosides 32 and 34, and the amino acids 43 and 47. Proton observe, 19F irradiated (1H-{19F}) NOE difference spectroscopy was used for the first time as an unequivocal method for the assignment of olefin geometry for fluorovinyl sulfones, (fluorovinyl)stannanes and fluoro olefins.
