17763-67-6 Usage
Description
Phenyl trifluoromethanesulfonate, also known as phenyl triflate, is an aryl fluorosulfonate that has been synthesized by the reaction of phenol with fluorosulfonic anhydride. It is a colorless liquid and is widely used in various chemical reactions and synthesis processes due to its reactivity and stability.
Uses
Used in Chemical Synthesis:
Phenyl trifluoromethanesulfonate is used as an arylating agent for the asymmetric α-arylation of ketones, catalyzed by Pd(dba)2 and difluorphos. This application is significant in the synthesis of various organic compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, phenyl triflate is used as a reactant in the one-pot synthesis of carbazoles. This process involves palladium-catalyzed N-arylation of anilines with phenyl triflate followed by oxidative coupling, which is crucial for the development of new drugs and therapeutic agents.
Used in Organic Chemistry Research:
Phenyl triflate is utilized in the synthesis of N-(2,6-diarylbenzoyl)anilines by diarylation of benzanilides with phenyl triflate in the presence of a palladium-based catalyst. This application is essential for the development of novel organic compounds with potential applications in various fields.
Used in Synthesis of Chiral Compounds:
Phenyl trifluoromethanesulfonate is employed as an arylating agent in the synthesis of (R)-2-phenyl-2,3-dihydrofuran by the arylation of 2,3-dihydrofuran. This process is vital for the production of chiral compounds, which are crucial in the pharmaceutical and chemical industries for their unique properties and applications.
Preparation
Synthesis of Phenyl trifluoromethanesulfonate: The reaction of phenol (1.00 g, 10.6 mmol) with triflic anhydride as outlined in the general procedure provided phenyl trifluoromethanesulfonate as colorless oil (0.73 g, 30%).1H NMR (400 MHz, CDCl3) δ 7.50 – 7.42 (m, 2H), 7.41 – 7.36 (m, 1H), 7.32 – 7.24 (m, 2H).
Check Digit Verification of cas no
The CAS Registry Mumber 17763-67-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,7,6 and 3 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 17763-67:
(7*1)+(6*7)+(5*7)+(4*6)+(3*3)+(2*6)+(1*7)=136
136 % 10 = 6
So 17763-67-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H5F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h1-5H
17763-67-6Relevant articles and documents
Effenberger,Mack
, p. 3947 (1970)
Dual Photoredox-/Palladium-Catalyzed Cross-Electrophile Couplings of Polyfluoroarenes with Aryl Halides and Triflates
Qin, Jian,Zhu, Shengqing,Chu, Lingling
supporting information, p. 2246 - 2252 (2021/04/02)
A visible-light photoredox-/Pd-catalyzed cross-electrophile arylation of polyfluoroarenes with aryl halides and triflates in the presence of dialkylamines is reported for the first time. This synergistic protocol affords access to a series of fluorodiaryls from easily available starting materials under mild and operationally simple conditions. A series of mechanistic experiments, including the stoichiometric reactions of a ligated (aryl)Pd complex, Stern-Volmer fluorescence quenching studies, cyclic voltammetry studies, and UV-vis spectroscopy, were performed to elucidate the potential catalytic pathway in this synergistic process.
Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones
Hallur, Gurulingappa,Suresh, Palaniswamy,Tamizharasan, Natarajan
supporting information, p. 12318 - 12325 (2021/09/07)
A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library.
Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates
Pospech, Jola,Taeufer, Tobias
, p. 7097 - 7111 (2020/06/27)
This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.
