A general method for the α-trifluoromethylthiolation of carbonyl compounds, without prefunctionalization, has been developed. Aldehydes, ketones, esters, amides, keto-esters, alkaloids, and steroids have been trifluoromethylthiolated with good yields. This work, proposing a new reagent for electrophilic trifluoromethylthiolation, provides a route towards the original synthesis of various trifluoromethylthiolated molecules for further applications.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201403409 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF-Substituted Indolines.
Org Lett
January 2025
School of Pharmacy, Hebei Medical University, Shijiazhuang 050017, China.
We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products.
View Article and Find Full Text PDFSynthesis and Electrophilic Trifluoromethylthiolation Properties of 1-Methyl-4-(trifluoromethylthio)piperazine (MTTP).
Org Lett
August 2024
Department of Chemistry, University of Louisville, 2320 S. Brook Street, Louisville, Kentucky 40292, United States.
A cyclic diamine, 1-methyl-4-(trifluoromethylthio)piperazine (MTTP, ), prepared by a one-step reaction from commercial materials, is a shelf-stable and powerful electrophilic trifluoromethylthiolating (CFS) reagent with wide reactivity profile. Activation of with triflic acid (TfOH) yields two reactive species and , depending on the molar ratios of TfOH/. showed unprecedented high reactivity, making possible the trifluoromethylthiolation of electron-deficient aromatic systems.
View Article and Find Full Text PDFEnantioselective α-Trifluoromethylthiolation of Carbonyl Compounds with AgSCF and Trichloroisocyanuric Acid.
J Org Chem
June 2024
School of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, P.R. China.
We successfully developed an enantioselective trifluoromethylthiolation of structurally diverse carbonyl compounds. Trichloroisocyanuric acid and AgSCF were employed to generate active electrophilic trifluoromethylthio species in situ for asymmetric C-SCF bond formation. A broad variety of chiral SCF-carbon nucleophiles (pyrazolones, β-keto esters, and β-keto amides) were obtained in excellent yields with high enantioselectivities (up to 92% ee) by Cinchona alkaloid derived squaramide catalysts.
View Article and Find Full Text PDFSynthesis of Fluorinated Amines: A Personal Account.
ACS Org Inorg Au
December 2023
Univ Lyon, CNRS, Université Claude Bernard Lyon 1, ICBMS, UMR 5246, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France.
This Account highlights the recent contributions made by our laboratory in the development of novel strategies to synthesize fluorinated amines. These strategies allow the practitioner to efficiently access carbamoyl fluorides, thiocarbamoyl fluorides as well as trifluoromethylamines using CO or CS as benign C1 sources. In addition, a novel N(SCF)CF moiety was synthesized.
View Article and Find Full Text PDFIntramolecular Heterocyclization/Fluoromethylthiolation of Alkynes Enabled by a Multicomponent Reagent System.
Org Lett
May 2023
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
The BnSR (R = CFH or CF)/CPBA/TfO system was found to be an effective multicomponent reagent system for the one-pot synthesis of di/trifluoromethylthiolated heterocycles from alkynes. The reaction was postulated to proceed via a cascade sequence involving the oxidation of BnSR by CPBA, activation of the in situ-generated sulfoxide by TfO, and intramolecular cyclization/fluoromethylthiolation of the alkyne substrates enabled by the formed electrophilic sulfonium salt to give di/trifluoromethylthiolated heterocycles.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!