88284-48-4

Usage

Uses

Used in Organic Synthesis:
2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for various organic synthesis applications, including reactions of polycyclic arenes, heteroatom arylation, heterocycles, and benzannulated heterocycles. Its reactivity allows for the formation of carbon-carbon and carbon-heteroatom bonds, making it a versatile tool in organic chemistry.
Used in Benzyne Generation:
2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for generating benzyne under mild conditions of simple fluoride treatment at room temperature. Benzyne is an important intermediate in organic synthesis, and its generation using this reagent allows for the formation of various functionalized aromatic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for the synthesis of various drug molecules. Its ability to form carbon-carbon and carbon-heteroatom bonds makes it useful in the development of novel pharmaceutical compounds with potential therapeutic applications.
Used in Material Science:
In material science, 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for the synthesis of functionalized polymers and materials. Its reactivity allows for the formation of various polymer structures with potential applications in areas such as electronics, sensors, and coatings.

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 18036-83-4 o-(trimethylsilyl)phenol trimethylsilyl ether 
• 36601-47-5 2-bromophenyl trimethylsilyl ether 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 15288-53-6 o-(trimethylsilyl)phenol 
• 17881-65-1 (2-chlorophenoxy)trimethylsilane 
• 95-57-8 2-monochlorophenol 
• 17878-37-4 1-bromo-2-(trimethylsilyl)benzene 
• 95-56-7 2-hydroxybromobenzene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 72525-60-1 hexamethyldisilazan 

Downstream Products

• 100-66-3 methoxybenzene 
• 101-84-8 diphenylether 
• 217-59-4 triphenylene 
• 15810-14-7 9,10-diethylphenanthrene 
• 602-15-3 9,10-diphenylphenanthrene 
• 751-38-2 1,2,3,4-tetraphenylnaphthalene 
• 15810-16-9 dimethyl 9,10-phenanthrenedicarboxylic acid 
• 36063-07-7 tetramethyl naphthalene-1,2,3,4-tetracarboxylate 
• 33498-62-3 9-methyl-10-phenylphenanthrene 
• 68684-64-0 9-ethyl-10-phenylphenanthrene 
• 605-05-0 9-benzyl-phenanthrene 
• 119-61-9 benzophenone 
• 79249-48-2 6-phenyl-6H-dibenzo[b,d]thiopyran 
• 883-20-5 9-methylphenanthrene 

Relevant academic research and scientific papers

Benzyne-Mediated Esterification Reaction

A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.

Benzyne 1,2,4-Trisubstitution and Dearomative 1,2,4-Trifunctionalization

Both 1,2,4-trisubstitution and dearomative 1,2,4-trifunctionalization of benzyne have been accomplished from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations proceed through a benzyne insertion into the S═O bond and an uncommon regiospecific anionic [4,5]-sigmatropic rearrangement, furnishing a C-O, C-S, and C-C bond on the C1-, C2-, and C4-position of a benzene ring, respectively. This study showcases new cascade benzyne reaction modes involving both distal C-H bond functionalization and dearomatization.

Stereoretentive Ring-Opening Metathesis Polymerization to Access All- cis Poly(p-phenylenevinylene)s with Living Characteristics

Poly(p-phenylenevinylene)s (PPVs), a staple of the conductive polymer family, consist of alternating alkene and phenyl groups in conjugation. The physical properties of this organic material are intimately linked to the cis/trans configuration of the alkene groups. While many synthetic methods afford PPVs with all-trans stereochemistry, very few deliver the all-cis congeners. We report herein a synthesis of all-cis PPVs with living characteristics via stereoretentive ring-opening metathesis polymerization (ROMP). Exquisite catalyst control allows for the preparation of homopolymers or diblock copolymers with perfect stereoselectivity, narrow dispersities, and predictable average molar masses. All-cis PPVs can then serve as light-responsive polymers through clean photoisomerization of the stilbenoid units.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Transition-Metal-Free Benzannulation of Tricarbonyl Derivatives with Arynes: Access to 1,3-Dinaphthol Precursors for the Synthesis of Rhodamine Dye Analogues

Herein, we report a transition-metal-free annulation reaction of benzynes and 1,3-oxopentanedioate for the synthesis of highly functionalized naphthalene derivatives for the first time. Additionally, the representative naphthalene derivatives have been successfully transformed into the new series of rhodamine dye analogues.

Access to Highly Functionalized Indanes from Arynes and α,γ-Diketo Esters

An unprecedented method for the synthesis of highly functionalized indanes from arynes and α,γ-diketo esters is described. Importantly, mild and nearly pH-neutral conditions ensure excellent functional group tolerance. Theoretical studies indicated that t

Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent

Fluorine is probably another favorite hetero-atom for incorporation into small molecules after nitrogen. Among many fluorine-containing groups, trifluoromethyl aryl ethers (ArOCF3) have unique properties in drug design and are difficult to be synthesized, and many different methods were developed to prepare them. A novel one-pot synthesis of o-iodine-aryl trifluoromethyl ethers (ArOCF3I) was described by the reaction of trifluoromethoxylation and iodination with trifluoromethyl aryl sulfonates (TFMS) in this manuscript. The reaction conditions were optimized by screening different solvents, crown ethers, substrates and the ratios and the yields of products were in moderate to high yields (up to 86%).

A facile route to 1: H- A nd 2 H-indazoles from readily accessible acyl hydrazides by exploiting a novel aryne-based molecular rearrangement

Herein we report the transformation of readily synthesised acyl hydrazides into 2-hydrazobenzophenones via a novel molecular rearrangement pathway using aryne chemistry. The developed reaction protocol is performed under relatively mild conditions and is

Tandem nucleophilic addition-cycloaddition of arynes with α-iminoesters: Two concurrent pathways to imidazolidines

The tandem nucleophilic addition-cycloaddition reaction has been developed for the synthesis of functionalized imidazolidine derivatives. A variety of α-iminoesters and aryne precursors were well tolerated under the mild reaction conditions. This asymmetric cycloaddition afforded imidazolidine derivatives with high yields, complete regioselectivities, and excellent diastereo- and enantioselectivities. Aryne-induced ylides working as 1,3-dipoles for asymmetric cycloaddition are the notable feature of the present reaction. In the tandem reaction, the [3+2] cycloaddition of aryne-induced ylides with metallized α-iminoesters and metal-catalyzed [3+2] cycloaddition of azomethine ylide with α-iminoesters are two concurrent pathways to imidazolidines.