28143-80-8

Usage

Uses

Used in Pharmaceutical Industry:
3-methylbut-2-en-2-yl trifluoromethanesulfonate is used as a reagent for the synthesis of pharmaceuticals, as its strong electrophilic properties and ability to form carbon-carbon and carbon-heteroatom bonds make it suitable for creating complex molecular structures.
Used in Agrochemical Industry:
3-methylbut-2-en-2-yl trifluoromethanesulfonate is used as a reagent in the synthesis of agrochemicals, where its versatility in forming various chemical bonds is beneficial for developing new and effective compounds for agricultural applications.
Used in Fine Chemicals Synthesis:
3-methylbut-2-en-2-yl trifluoromethanesulfonate is used as a reagent for the synthesis of fine chemicals, taking advantage of its electrophilic nature and ability to participate in nucleophilic substitution and elimination reactions to create a wide range of specialized chemical products.
Used as a Fluorine Source:
3-methylbut-2-en-2-yl trifluoromethanesulfonate is used as a fluorine source in various chemical reactions, providing a convenient and effective way to introduce fluorine atoms into organic molecules.

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 78-80-8 2-methylbut-1-en-3-yne 

Downstream Products

• 128925-79-1 (3-methyl-2-buten-2-yl)triphenylphosphonium triflate 
• 52776-41-7 2,3-dimethyl-1-phenyl-2-butene-1-one 

Relevant academic research and scientific papers

Ionic Hydrogenation of Alkynes by HOTf and Cp(CO)3WH

Alkynes can be hydrogenated at room temperature by an ionic hydrogenation method using triflic acid (CF3SO3H) as the proton donor and a transition metal hydride (Cp(CO)3WH) as the hydride donor.Reaction of PhCCH with HOTf and Cp(CO)3WH gives ethylbenzene as the final product in high yield.Intermediate observed in this reaction are the vinyl triflate CH2=C(Ph)(OTf) and the geminal ditriflate Ph(CH3)C(OTf)2, which result from the addition of 1 or 2 equiv of HOTf to the CC triple bond of the alkyne.Hydrogenation of PhCCMe by HOTf and Cp(CO)3WH similarly produces propylbenzene as the ultimate product.Along with vinyl triflates, additional intermediates observed in this reaction were the cis and trans isomers of the β-methylstyrene complex 2-PhHC=CHCH3)>(+)(-).Hydrogenation of n-butylacetylene to n-hexane does occur upon reaction with HOTf/Cp(CO)3WH, but is very slow.In the absence of metal hydrides, 2-methyl-1-buten-3-yne reacts with HOTf to give the vinyl triflate CH2=CMeC(OTf)=CH2, but reaction with HOTf and Cp(CO)3WH gives Me2C=C(OTf)Me.The key characteristics required for the metal hydride used in these hydrogenations are the ability to donate hydride in the presence of strong acid, and the absence of rapid decomposition of the hydride through reaction with the strong acid.Cp(CO)3WH meets these requirements, but HSiEt3, while an effective hydride donor, is decomposed by HOTf on the time scale of these alkyne hydrogenation reactions.

On the Mechanism of the Metal Mediated Vinylic Cross Coupling Reactions. 1. Oxidative Addition: The Reaction of Vinyl Triflates with Zerovalent Platinum. Kinetics, Stereochemistry, and Molecular Structure

The oxidative addition reaction of alkylvinyl triflates with (Ph3P)4Pt and (Ph3P)2Pt(C2H4) was investigated as a prototypical example of the first step of the Ni triad metal mediated vinylic cross coupling reactions.Kinetic, stereochemical, and variable temperature NMR experiments were carried out to establish the involvement of ?-alkene complexes in these reactions.The proposed mechanism involves rate-determining formation of a ?-alkene Pt complex, followed by rapid rearrangement to a ?-vinyl triflato-Pt(II) complex, and then addition of PPh3 to yield a ?-vinylcationic Pt(II) complex.Both ?-vinyl complexes were isolated and fully characterized, as stable crystalline species.A single crystal molecular structure determination is reported for the ?-(trans-2-butenyl)tris(triphenylphosphine)platinum(II) triflate complex.