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Transition-Metal-Free Thioboration of Terminal Alkynes.
JACS Au
December 2024
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
We present a new type of elementoboration reaction, the thioboration of terminal alkynes. This method enables highly controllable regio-/stereo-/chemoselective - and -thioboration on demand, affording synthetically versatile and densely functionalized vinyl boron/vinyl sulfide derivatives in a straightforward manner without the need for a transition-metal catalyst.
View Article and Find Full Text PDFB(CF)-Catalyzed Regiodivergent Thioetherifications of Alkenes via Thiiranium Intermediates: Experimental and Computational Insights.
Chemistry
December 2024
Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Translational Research Hub, Maindy Road, Cathays, Cardiff, Cymru/Wales, CF24 4HQ, UK.
Precise control of selective alkene functionalization is a continuing challenge in the chemical community. In this study, we develop a substitution-controlled regiodivergent thioetherification of di- or trisubstituted alkenes using 10 mol % tris(pentafluorophenyl)borane [B(CF)] as a catalyst and N-thiosuccinimide as a sulfenylating reagent. This metal-free borane catalyzed C-S bond forming method is utilized for a Csp-H sulfenylation reaction to synthesize an array of diphenylvinylsulfide derivatives with good to excellent yields (25 examples, up to 91 % yield).
View Article and Find Full Text PDFSelective Synthesis of Vinyl Sulfides or 2-Methyl Benzothiazoles from Disulfides and CaC Mediated by a Trisulfur Radical Anion.
J Org Chem
December 2024
College of Chemical Engineering, Inner Mongolia University of Technology, Hohhot 010051, China.
In this report, we have established a novel and efficient method for selectively synthesizing either vinyl sulfides or 2-methylbenzothiazoles from the reaction of CaC and disulfides. The selective synthesis of these two distinct products can be controlled by simply adjusting the amount of KS. The underlying reaction mechanism has been thoroughly investigated through control experiments, HRMS, and FTIR, which collectively support the pivotal role of a trisulfur radical anion.
View Article and Find Full Text PDFHydrogen Isotope Labeling of Pharmaceuticals Via Dual Hydrogen Isotope Exchange Pathways Using CdS Quantum Dot Photocatalyst.
J Am Chem Soc
December 2024
Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112, United States.
Isotopic labeling is a powerful technique extensively used in the pharmaceutical industry. By tracking isotope-labeled molecules, researchers gain unique and invaluable insights into the pharmacokinetics and pharmacodynamics of new drug candidates. Hydrogen isotope labeling is particularly important as hydrogen is ubiquitous in organic molecules in biological systems, and it can be introduced effectively through late-stage hydrogen isotope exchange (HIE).
View Article and Find Full Text PDFThanatin and vinyl sulfide analogues as narrow spectrum antimicrobial peptides that synergise with polymyxin B.
Front Pharmacol
November 2024
School of Chemical Sciences, The University of Auckland, Auckland, New Zealand.
Thanatin is a β-hairpin antimicrobial peptide cyclised by a single disulfide bond that has shown potent broad-spectrum activity towards bacterial and fungal pathogens. Towards Gram-negative species, thanatin acts both by forming trans-membranal pores and inhibiting outer membrane biogenesis by binding to LptA and blocking lipopolysaccharide (LPS) transport. Inspired by previous modifications of thanatin, an analogue was prepared which demonstrated potent but selective activity towards .
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