128373-13-7

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indol-5-yl trifluoromethanesulfonate is used as a key intermediate for the synthesis of various pharmaceuticals, including drugs with potential applications in the treatment of various diseases and disorders. Its unique reactivity and properties make it a valuable building block in the development of new therapeutic agents.
Used in Agrochemical Industry:
1H-Indol-5-yl trifluoromethanesulfonate is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, to improve crop protection and yield. Its versatile reactivity allows for the development of novel compounds with enhanced efficacy and selectivity.
Used in Materials Science:
1H-Indol-5-yl trifluoromethanesulfonate is used as a component in the development of new materials with potential applications in various industries, such as electronics, coatings, and polymers. Its unique properties and reactivity contribute to the creation of innovative materials with improved performance characteristics.
Used in Organic Synthesis:
1H-Indol-5-yl trifluoromethanesulfonate is used as a reagent in organic synthesis for the introduction of the trifluoromethanesulfonate group onto various substrates. This allows for the creation of new compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C9H6F3NO3S/c10-9(11,12)17(14,15)16-7-1-2-8-6(5-7)3-4-13-8/h1-5,13H

Upstream product

• 1953-54-4 indol-5-ol 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 1493-13-6 trifluorormethanesulfonic acid 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 66616-72-6 5-phenyl-1H-indole 
• 10075-50-0 5-bromo-1H-indole 

Relevant academic research and scientific papers

SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates

Sulfur(vi) Fluoride Exchange (SuFEx) chemistry has emerged as a next-generation click reaction, designed to assemble functional molecules quickly and modularly. Here, we report the ex situ generation of trifluoromethanesulfonyl fluoride (CF3SO2F) gas in a two chamber system, and its use as a new SuFEx handle to efficiently synthesize triflates and triflamides. This broadly tolerated protocol lends itself to peptide modification or to telescoping into coupling reactions. Moreover, redesigning the SVI-F connector with a SO → SNR replacement furnished the analogous triflimidoyl fluorides as SuFEx electrophiles, which were engaged in the synthesis of rarely reported triflimidate esters. Notably, experiments showed H2O to be the key towards achieving chemoselective trifluoromethanesulfonation of phenols vs. amine groups, a phenomenon best explained - using ab initio metadynamics simulations - by a hydrogen bonded termolecular transition state for the CF3SO2F triflylation of amines. This journal is

Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage

A nickel-catalyzed reductive coupling of aryl triflates with thiocarbonates is reported here. Both electron-rich and -deficient aryl C(sp2)-O electrophiles as well as a class of O-tBu S-alkyl thiocarbonates are compatible with the optimized reaction conditions, as evidenced by 49 examples. The reaction also proceeds with good chemoselective cleavage of the C-O bond with regard to thioesters. This work broadens the scope of nickel-catalyzed reductive cross-electrophile coupling reactions.

Selective arylation and vinylation at the α position of vinylarenes

In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion. What the Heck! In intermolecular Heck reactions, insertion at the β position of aromatic olefins is very common, but reversal of the selectivity for selective α insertion has been a longstanding problem. A general method to couple aryl and vinyl triflates with aromatic olefins in >20:1 α selectivity is presented. The key to this successful approach is a new ferrocene bisphosphane with naphthyl groups on the phosphorus atom (see scheme; OTf=triflate). Copyright

Intermolecular mizoroki-heck reaction of aliphatic olefins with high selectivity for substitution at the internal position

New ligand for old reaction: The title reaction of aryltriflates with aliphatic olefins leads to substitution at the internal position with high selectivity. The ratio of the desired isomer (shown in the scheme) to the sum of all other isomers is generall

Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates

Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.