α-(Difluoromethyl)styrene: Improved approach to grams scale synthesis

Walkowiak-Kulikowska, Justyna; Kanigowska, Joanna; Koroniak, Henryk

doi:10.1016/j.jfluchem.2015.07.008

Cited by 10 publications

(4 citation statements)

References 14 publications

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“…[7h, 11] Theu nrealized potential of HVI-mediated fluorination is with structural classes where deoxygenative fluori-nation strategies are unknown. Although a-(difluoromethyl)styrenes are precursors to polysubstituted fluoroalkene, [12] and novel fluorinated polymers, [13,14] there are no deoxyfluorination strategies reported for these species. [15] They have been prepared by direct fluorination using cesium fluoroxysulfate (CsSO 4 F), [16] however,t he typical approach involves olefination [12,17] or dehydration [13,18] of af luorinecontaining precursor.W eaimed to develop adirect synthesis of a-(difluoromethyl)styrenes through aT olIF 2 -mediated fluorinative rearrangement of phenylallene derivatives.…”

mentioning

confidence: 99%

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α‐(Difluoromethyl)styrenes

Zhao,

Racicot,

Murphy

2017

Angew Chem Int Ed

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Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo)toluene in the presence of 20 mol % BF ⋅OEt to yield α-difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene π bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl- and α-allenyl substituents, and diphenylallenes were investigated, and good functional-group compatibility was observed throughout. The ease with which allenes can be prepared on a large scale, and the operational simplicity of this reaction allowed us to rapidly access fluorine-containing building blocks that have not been accessed by conventional deoxyfluorination strategies.

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confidence: 99%

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α‐(Difluoromethyl)styrenes

Zhao,

Racicot,

Murphy

2017

Angew Chem Int Ed

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“…Synthesis of a-(diuoromethyl)styrene (DFMST) a-(Diuoromethyl)styrene (DFMST) was successful synthesized according to literature procedure. 43 In the synthesis of targeted monomer the following three-step route (Scheme 1) was employed: (i) a base-induced diuoromethylation coupling with PhSO 2 CF 2 H as selective "CF 2 H À " equivalent allowed to introduce diuoromethyl function, (ii) the reductive desulfonylation and subsequent (iii) dehydration. The synthetic route was implemented for grams scale preparation of the DFMST in 56% overall yield.…”

Section: Resultsmentioning

confidence: 99%

“…Non-commercial fluorinated monomer, α-(difluoromethyl)-styrene (DFMST), was synthesized according to literature procedure (ESI, Section 1 † ). 43 …”

Section: Methodsmentioning

confidence: 99%

“…[40][41][42] Previously, we presented the cost-effective and grams scale synthesis of DFMST. 43 Since our objective is to examine the inuence of the uorine content of styrenic monomers on both reactivity and copolymer composition, it was of interest to thoroughly study the behaviour of DFMST in radical copolymerization. Furthermore, the resulting novel FAPs possessing diuoromethyl styrenic units were evaluated in terms of its thermal and surface properties.…”

Section: Introductionmentioning

confidence: 99%

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Aromatic fluorocopolymers based on α-(difluoromethyl)styrene and styrene: synthesis, characterization, and thermal and surface properties

et al. 2018

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Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α‐(Difluoromethyl)styrenes

2017

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Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo)toluene in the presence of 20 mol % BF3⋅OEt2 to yield α‐difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene π bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl‐ and α‐allenyl substituents, and diphenylallenes were investigated, and good functional‐group compatibility was observed throughout. The ease with which allenes can be prepared on a large scale, and the operational simplicity of this reaction allowed us to rapidly access fluorine‐containing building blocks that have not been accessed by conventional deoxyfluorination strategies.

show abstract

α-(Difluoromethyl)styrene: Improved approach to grams scale synthesis

Cited by 10 publications

References 14 publications

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α‐(Difluoromethyl)styrenes

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α‐(Difluoromethyl)styrenes

Aromatic fluorocopolymers based on α-(difluoromethyl)styrene and styrene: synthesis, characterization, and thermal and surface properties

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α‐(Difluoromethyl)styrenes

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