Hiyama coupling reaction of fluorous alkenyl-fluorosilanes: Scope and mechanistic considerations

Csapó, Ágnes; Bodor, Andrea; Rábai, József

doi:10.1016/j.jfluchem.2012.03.007

Cited by 5 publications

(2 citation statements)

References 40 publications

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“…The product 5l was purified with silica gel chromatography (petroleum ether) as a colorless oil (84.6 mg, 81% yield, E / Z > 99:1). Analytical data for 5l was consistent with that previously reported …”

Section: Methodsmentioning

confidence: 99%

“…The incorporation of fluorine into organic molecules has long been an important strategy in medicinal chemistry . Along with the intensive studies and advances reported on the fluoroalkylation of aromatic compounds, the construction of C vinyl –C Rf bonds has also been achieved in recent decades . Decarboxylative coupling reactions catalyzed by transition metals have attracted significant attention in synthetic organic chemistry and have emerged as valuable tools for the construction of carbon–carbon bonds .…”

Section: Introductionmentioning

confidence: 99%

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Copper-Catalyzed Decarboxylative Difluoroalkylation and Perfluoroalkylation of α,β-Unsaturated Carboxylic Acids

2016

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Copper-catalyzed decarboxylative difluoroalkylation and perfluoroalkylation of α,β-unsaturated carboxylic acids is described. Promoted by dialkyl phosphite, this novel reaction affords fluoroalkylated motifs with excellent stereoselectivity and broad substrate scope under mild reaction conditions from readily available fluoroalkyl iodides and bromides. Preliminary mechanism study suggests that radical pathway was involved in the catalytic cycle and dialkyl phosphite had played an indispensable role in this reaction.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Decarboxylative Difluoroalkylation and Perfluoroalkylation of α,β-Unsaturated Carboxylic Acids

2016

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ChemInform Abstract: Hiyama Coupling Reaction of Fluorous Alkenyl‐fluorosilanes: Scope and Mechanistic Considerations.

2012

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Novel fluorous alkenyl-fluorosilanes (V) are synthesized by a three-step procedure and subjected to a Hiyama coupling reaction with iodobenzene to provide the appropriate ω-perfluoroalkyl-styrenes. In general, the reaction of (Va) with o-substituted iodobenzene fails, while m-and p-substituted iodobenzenes give rise to formation of fluorous styrenes in low to high yields. The mechanism of the coupling reaction is a pure Hiyama-type one involving fluoride-ion induced transmetalation without Heck-type contribution. -(RABAI*, J.; CSAPO, A.; BODOR, A.; J. Fluorine Chem. 137 (2012) 85-92, http://dx.

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Siloxane based syntheses of fluorous ethenes and their tandem Heck reactions with aryl iodides

Csapó

Rábai

2012

Journal of Fluorine Chemistry

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Hiyama coupling reaction of fluorous alkenyl-fluorosilanes: Scope and mechanistic considerations

Cited by 5 publications

References 40 publications

Copper-Catalyzed Decarboxylative Difluoroalkylation and Perfluoroalkylation of α,β-Unsaturated Carboxylic Acids

Copper-Catalyzed Decarboxylative Difluoroalkylation and Perfluoroalkylation of α,β-Unsaturated Carboxylic Acids

ChemInform Abstract: Hiyama Coupling Reaction of Fluorous Alkenyl‐fluorosilanes: Scope and Mechanistic Considerations.

Siloxane based syntheses of fluorous ethenes and their tandem Heck reactions with aryl iodides

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