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Synthesis of Pentafluorosulfanylated Ynamides and Further Functionalizations.
Org Lett
December 2024
Université de Haute-Alsace, Université de Strasbourg, CNRS, LIMA, UMR 7042, 68000 Mulhouse, France.
Article Synopsis
- The article presents the first successful creation of SF-ynamides, which are multifunctional compounds incorporating a pentafluorosulfanyl group.
- * The synthesis involves a two-step process: first, a radical reaction adds the SF group to different terminal ynamides, followed by removing a chlorine atom.
- * Various chemical reactions can readily modify these newly formed SF-ynamides, demonstrating their potential for diverse applications in organic chemistry.
Catalytic enantioselective synthesis of 2-pyrazolines one-pot condensation/6Ï€-electrocyclization: 3,5-bis(pentafluorosulfanyl)-phenylthioureas as powerful hydrogen bond donors.
Chem Sci
August 2024
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida Gainesville Florida 32611 USA
A new conjugate-base-stabilized carboxylic acid (CBSCA) containing a 3,5-bis(pentafluorosulfanyl)phenylthiourea functionality catalyses challenging one-pot condensations/6π-electrocyclizations of hydrazines and α,β-unsaturated ketones under mild conditions. Structurally diverse -aryl 2-pyrazolines are obtained in good yields and enantioselectivities. The superior performance of 3,5-bis(SF)phenylthioureas over the widely used 3,5-bis(CF)phenylthioureas is further demonstrated in the Michael addition of dimethyl malonate to nitrostyrene, using a new Takemoto-type catalyst.
View Article and Find Full Text PDFHydrothiolation of Triisopropylsilyl Acetylene Sulfur Pentafluoride - Charting the Chemical Space of β-SF Vinyl Sulfides.
Chempluschem
August 2024
Department of Chemistry and Applied Biosciences Zürich, Vladimir-Prelog-Weg 2, CH-8093, Zürich, Switzerland.
Recently, we suggested liquid and high-boiling TIPS-CC-SF (TASP) as a versatile reagent to access so far elusive SF-containing building blocks by less specialized laboratories under bench-top conditions. The synthesis of non-aromatic SF building blocks generally requires on-site fluorination or pentafluorosulfanylation steps employing toxic and/or gaseous reagents. Herein, we underline the versatility of this reagent by reporting a benign bench-top protocol for the synthesis of Z-configured β-pentafluorosulfanylated vinyl sulfides in good to excellent yields (up to 99 %) with exclusive (Z)-diasteroselectivity and broad functional group tolerance.
View Article and Find Full Text PDFPentafluorosulfanyl-substituted biaryl derivatives as MATE-type transporter inhibitors targeting drug-resistant bacteria.
Bioorg Med Chem
February 2024
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
Multidrug and toxin extrusion (MATE) inhibitors improve the antimicrobial susceptibility of drug-resistant bacteria by preventing the efflux of administered antibiotics. In this study, we optimized the chemical structure of a previously identified bacterial-selective MATE inhibitor 1 (EC > 30 µM) to improve its activity further. Compound 1 was divided into three fragments (aromatic part, linker part, and guanidine part), and each part was individually optimized.
View Article and Find Full Text PDFTransition-Metal-Free Approach for Z-Vinyl Fluorides by Hydrofluorination of Alkynes bearing SF and SF Groups.
Angew Chem Int Ed Engl
March 2024
Department of Life Science and Applied Chemistry, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
The synthesis of vinyl fluorides plays a crucial role in various scientific disciplines, including pharmaceutical and materials sciences. Herein, we present a direct and stereoselective hydrofluorination method for the synthesis of Z isomers of vinyl fluorides from alkynes containing unexplored SF and SF groups. Our strategy employed tetrabutylammonium fluoride (TBAF) as a fluorine source.
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