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Usage

Uses

Used in Organic Synthesis:
6,7-DIHYDRO-2-PENTAFLUOROPHENYL-5H-PYRROLO(2,1-C)-1,2,4-TRIAZOLIUM TETRAFLUOROBORATE, 97% is used as a catalyst for intermolecular homodimerization of aryl aldehydes. It facilitates the reaction by activating the aldehyde group, leading to the formation of symmetrical diarylmethanols.
Used in Benzoin Cyclizations:
In the pharmaceutical industry, 6,7-DIHYDRO-2-PENTAFLUOROPHENYL-5H-PYRROLO(2,1-C)-1,2,4-TRIAZOLIUM TETRAFLUOROBORATE, 97% is used as a catalyst for intramolecular aldehyde-ketone benzoin cyclizations. This reaction is crucial for the synthesis of various biologically active compounds, including natural products and pharmaceutical agents.
Used in Stetter Reactions:
6,7-DIHYDRO-2-PENTAFLUOROPHENYL-5H-PYRROLO(2,1-C)-1,2,4-TRIAZOLIUM TETRAFLUOROBORATE, 97% is also used as a catalyst for intramolecular Stetter reactions. This reaction involves the coupling of an aldehyde with an activated alkene, resulting in the formation of functionalized cyclohexenes. It is an important method for the synthesis of complex molecular architectures in the pharmaceutical and agrochemical industries.

Reaction

Reagent used in the highly enantioand diastereoselective, catalytic intramolecular Stetter reaction. Enantioselective synthesis of β-hydroxy and β-amino esters. Organocatalytic iminium ion/carbene reaction cascade for the formation of 2,4-disubstituted cyclopentenones. Synthesis of alloand epi-Inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes

Upstream product

• 616-45-5 2-pyrrolidinon 
• 122-51-0 orthoformic acid triethyl ester 
• 828-73-9 pentafluorophenyl hydrazine 
• 420-37-1 trimethoxonium tetrafluoroborate 

Relevant academic research and scientific papers

Selective Synthesis of Acylated Cross-Benzoins from Acylals and Aldehydes via N-Heterocyclic Carbene Catalysis

The utility of acylals as building blocks for selective cross-benzoin synthesis was explored in this study. The synthesis of α-acetoxyketones (O-acyl cross-benzoins) was achieved via selective N-heterocyclic carbene-catalyzed cross-benzoin reactions using acylals as aldehyde equivalents. Thus, the combination of ortho-substituted phenyl acylals and aromatic/aliphatic aldehydes as coupling substrates using bicyclic triazolium salts as precatalysts and potassium carbonate as a base in THF at reflux temperature selectively yielded O-acyl cross-benzoins.

The catalytic versatility of low toxicity dialkyltriazolium salts: In situ modification facilitates diametrically opposed catalysis modes in one pot

The ability of triazolium salts to serve as a precatalyst for both an acid and a powerful base/nucleophile (controlled by additives) has been exploited in a process characterised by a unique in situ catalyst modification strategy. The Royal Society of Chemistry 2013.

Metal-free, aerobic dioxygenation of alkenes using hydroxamic acids

(Chemical equation presented) One dioxygenation please, hold the metal: In the presence of either oxygen or air as the sole oxidant and external oxygen atom source, a variety of unsaturated hydroxamic acids afford cyclic hydroxamates that are readily converted into 1,2-diols, with the potential for high levels of reaction stereocontrol.

Probing the efficiency of N-heterocyclic carbene promoted O- to C-carboxyl transfer of oxazolyl carbonates

(Chemical Equation Presented) Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.

An efficient synthesis of achiral and chiral 1,2,4-triazolium salts: Bench stable precursors for N-heterocyclic carbenes

The promising utility of triazolyl N-heterocyclic carbene catalysts in umpolung aldehyde chemistry requires a straight-forward reliable synthesis from readily available materials. Herein, we describe the synthesis of a variety of triazolyl N-heterocyclic