The (benzenesulfonyl)difluoromethylsulfanyl (PhSO2CF2S) group is a valuable substituent with specific properties which can provide access to new applications of fluoroalkylthiolated compounds. Direct introduction of this moiety can be performed by in an electrophilic manner by using a new shelf-stable reagent, namely a (benzenesulfonyl)difluoromethanesulfenamide. Furthermore, mild magnesium-mediated reduction of the PhSO2CF2S group leads to a facile synthesis of difluoromethylthiolated molecules and their deuterated analogs.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201601280 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Direct trifluoromethylselenolations of electron-rich (hetero)aromatic rings with -trifluoromethylselenolating saccharin.
Org Biomol Chem
September 2024
College of Chemistry and Material Science, Shandong Agricultural University, Tai'an, Shandong 271018, P. R. China.
A novel, easily synthesizable, shelf-stable electrophilic trifluoromethylselenolating reagent, -trifluoromethylselenosaccharin, has been developed. This reagent can be synthesized in good yield by a two-step one-pot reaction from BnSeCF, SOCl, and silver saccharin. -Trifluoromethylselenosaccharin proves to be an efficient trifluoromethylselenolating reagent, enabling the direct trifluoromethylselenolation of various electron-rich aromatic and heteroaromatic rings under mild reaction conditions.
View Article and Find Full Text PDFEnabling Universal Access to Rapid and Stable Tetrazine Bioorthogonal Probes through Triazolyl-Tetrazine Formation.
JACS Au
August 2024
Department of Radiology and Huaxi MR Research Center, Functional and Molecular Imaging Key Laboratory of Sichuan Province and Frontiers Science Center for Disease Related Molecular Network, West China Hospital, Sichuan University, Chengdu 610041, China.
Despite the immense potential of tetrazine bioorthogonal chemistry in biomedical research, the in vivo performance of tetrazine probes is challenged by the inverse correlation between the physiological stability and reactivity of tetrazines. Additionally, the synthesis of functionalized tetrazines is often complex and requires specialized reagents. To overcome these issues, we present a novel tetrazine scaffold-triazolyl-tetrazine-that can be readily synthesized from shelf-stable ethynyl-tetrazines and azides.
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 PDFDecoupling Fluorous Protein Coatings Yield Heat-Stable and Intrinsically Sterile Bioformulations.
ACS Appl Mater Interfaces
July 2024
Department of Biomedical Engineering, Pennsylvania State University, University Park, Pennsylvania 16802-4400, United States.
Thermal inactivation is a major bottleneck to the scalable production, storage, and transportation of protein-based reagents and therapies. Failures in temperature control both compromise protein bioactivity and increase the risk of microorganismal contamination. Herein, we report the rational design of fluorochemical additives that promiscuously bind to and coat the surfaces of proteins to enable their stable dispersion within fluorous solvents.
View Article and Find Full Text PDFNFC-enabled photothermal-based microfluidic paper analytical device for glucose detection.
Analyst
July 2024
Department of Electrical and Computer Engineering, Tufts University, Medford, MA 02155, USA.
This study introduces the development of a photothermal-based microfluidic paper analytical device (PT-µPAD) integrated with near-field communication (NFC) technology and smartphone readout for enzyme-free glucose quantification in human samples. With the properties of gold nanoparticles (AuNPs) both as a nanozyme and as a photothermal substrate, there is no need for costly reagents like enzymes or a readout instrumentation for the selective and sensitive detection of glucose. In PT-µPADs, AuNPs are etched by hydrogen peroxide (HO) generated from glucose catalysis.
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!