Synthesis of Fluoroolefins via Julia-Kocienski Olefination

Zajc, Barbara; Kumar, Rakesh

doi:10.1055/s-0029-1218789

Cited by 108 publications

(46 citation statements)

References 47 publications

(88 reference statements)

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“…[8] In this respect, the JuliaKocienski reaction offers an attractive one-step access to fluoroalkylidenes. [30,31] Although both aldehydes and ketones are described as substrates, reactions that involve π-deficient heterocyclic fluorosulfones are most popular with functionalized aldehydes. The use of substituted ketones is rare because competitive reactions occur with substituted ketones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Fluorine‐Containing 3,3‐Disubstituted Oxetanes and Alkylidene Oxetanes

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Synthesis of Fluorine‐Containing 3,3‐Disubstituted Oxetanes and Alkylidene Oxetanes

et al. 2015

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“…Installation of the fluorine atom in the α‐position was carried out by deprotonation with sodium bis(trimethylsilyl)amide (NaHMDS) at −78 °C, followed by a reaction with N ‐fluorodibenzenesulfonimide (NFSI) in toluene. Different bases gave product 9 in lower or negligible yield, and the use of THF as a solvent led to oxidation of the starting material into the corresponding α,β‐unsaturated ketone, presumably through a single‐electron transfer (SET) mechanism …”

Section: Resultsmentioning

confidence: 99%

Fluorine‐Substituted Molecular Motors with a Quaternary Stereogenic Center

Štacko

Kistemaker

Feringa

2017

Chemistry A European J

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A series of unprecedented second generation molecular motors featuring a quaternary stereogenic center substituted with a fluorine atom has been synthesized. It is demonstrated that a seemingly benign replacement of the stereogenic hydrogen for a fluorine atom, regarded as a common substituent in pharmacology, resulted in a dramatic change in the energetic profile of thermal helix inversion. The barrier for the thermal helix inversion was found to increase considerably (by 20-30 kJ mol ), presumably due to destabilization of the transition state by increased steric hindrance when the fluorine atom is forced to pass over the lower half of the motor. This results in the activation barrier for the thermal helix inversion to be higher than the barrier for backward thermal E-Z isomerization, impairing the motor function. A fluorine-substituted motor capable of performing unidirectional rotation is successfully prepared when these limitations are considered in the design phase.

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“…In addition synthesis of fluoro enynes can be accomplished by using a novel a-fluoro-1,3-benzothiazol-2-yl propargyl sulfone [11]. A recent comprehensive article covers various aspects of Julia-Kocienski reaction for the synthesis of fluorooelfins [12].…”

Section: Introductionmentioning

confidence: 99%