28075-51-6

Usage

Functional groups

Trifluoromethylsulfonyloxy group

Reactivity

Highly reactive

Versatility

Versatile building block in organic synthesis

Applications

Preparation of various organic compounds

Chemical reactions

Useful in additions, eliminations, and substitution reactions

Electron-withdrawing property

Strong electron-withdrawing group

Leaving group property

Strong leaving group

Fields of application

Medicinal chemistry, agrochemical synthesis, materials science, fine chemicals, and pharmaceuticals

Current status

Actively studied and utilized in the field of organic chemistry

InChI:InChI=1/C8H11F3O3S/c9-8(10,11)15(12,13)14-7-5-3-1-2-4-6-7/h5H,1-4,6H2

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 502-42-1 cycloheptanone 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 22081-48-7 (cyclohept-1-en-1-yloxy)(trimethyl)silane 
• 7143-01-3 Methanesulfonic anhydride 
• 108-94-1 cyclohexanone 

Downstream Products

• 32960-45-5 1-(4-methoxyphenyl)cyclohept-1-ene 
• 98558-52-2 2-oxo-1-cycloheptanecarboxylate 
• 55110-62-8 1-(2-phenylethynyl)cycloheptene 
• 287944-13-2 2-(cyclohept-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1030239-96-3 C₁₁H₁₆O 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 440368-89-8 cyclohept-1-enyl-(4-methoxy-phenyl)-methanone 
• 25308-75-2 1-Phenylcycloheptene 
• 1161082-91-2 C₅₀H₈₂O₅Si₃ 
• 1161082-89-8 C₅₁H₈₆O₆Si₃ 
• 49565-03-9 (E)-1-iodocyclohept-1-ene 
• 13294-30-9 1-chlorocycloheptene 
• 18317-64-1 1-bromocycloheptene 
• 1289620-59-2 4-(4-cyclohept-1-en-1-ylphenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide 

Relevant academic research and scientific papers

Visible-Light Photoredox Catalyzed Dehydrogenative Synthesis of Allylic Carboxylates from Styrenes

The visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids is documented. The methodology enables the chemo- and regioselective allylic functionalization of styryl compounds, leading to allylic carboxylates (32 examples) under stoichiometric acceptorless conditions. Intermolecular as well as intramolecular variants are documented in high yields (up to 82%). A mechanistic rationale is also proposed on the basis of a combined experimental and spectroscopic investigation.

Alkenylation and Arylation of Peptides via Ni-Catalyzed Reductive Coupling of α- C-Tosyl Peptides with Csp2Triflates/Halides

A Ni-catalyzed reductive cross-coupling between α-C-tosyl peptides and Csp2 triflates/halides has been developed. This protocol enables the formation of various unnatural di- and tripeptides containing vinyl and aryl side chains, and it expands the applications of Ni-catalyzed reductive cross-coupling in late-stage diversification of peptides.

Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes

Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.

Catalytic allylic oxidation to generate vinylogous acyl sulfonates from vinyl sulfonates

Regioselective formation of vinylogous acyl sulfonates was accomplished via the allylic oxidation of the corresponding vinyl sulfonates. The reaction progressed through the agency of catalytic iron(III) chloride catalysis with tert-Butyl hydroperoxide (TBHP) as the stoichiometric oxidant. Tolerance of other functional groups, including some other allylic and benzylic sites, was observed.

Pd-Catalyzed Carbonylation of Vinyl Triflates to Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions

An efficient and general protocol for the synthesis of α,β-unsaturated aldehydes, esters, and amides via carbonylation of vinyl triflates including derivatives of camphor, ketoisophorone, verbenone, and pulegone was developed. Crucial for these transformations is the use of a specific palladium catalyst containing a pyridyl-substituted dtbpx-type ligand. This procedure also allows for an easy access of dicarbonylated products from the corresponding ketones.

Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents

A series of low-molecular-weight, compact, and multifunctional cyclic alkenylsulfonyl fluorides were efficiently prepared from the corresponding alkenyl triflates. Palladium-catalyzed sulfur dioxide insertion using the surrogate reagent DABSO effects sulfinate formation, before trapping with an F electrophile delivers the sulfonyl fluorides. A broad range of functional groups are tolerated, and a correspondingly large collection of derivatization reactions are possible on the products, including substitution at sulfur, conjugate addition, and N-functionalization. Together, these attributes suggest that this method could find new applications in chemical biology.

Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling to Form Highly Substituted 1,3-Dienes

The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5′-bis(trifluoromethyl)-2,2′-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.

Dual Gold-Catalyzed Formal Tetradehydro-Diels–Alder Reactions for the Synthesis of Carbazoles and Indolines

This work reports a dual gold-catalyzed tetradehydro-Diels–Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels–Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 π electrocyclization, followed with 1,2-hydrogen shift.

Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to α-Trifluoromethyl Ketones

We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of α-CF3ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3radical fr

Generation of cycloalkynes through deprotonation of cyclic enol triflates with magnesium bisamides

Deprotonative generation of cyclohexynes, cycloheptynes, and cyclooctynes was achieved by controlling the reactivities of transient anionic species from the corresponding enol triflates with magnesium bis(2,2,6,6-tetramethylpiperidide) as a base. The star