A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.4c01786 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation.
J Org Chem
September 2024
Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, School of Flexible Electronics (Future Technologies), Nanjing Tech University, Nanjing 211816, China.
A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.
View Article and Find Full Text PDFCobalt-Catalyzed Reductive Cross-Coupling To Construct Csp-Csp Bonds via Csp-S and Csp-X Bonds Activation.
Org Lett
October 2023
Laboratoire de Chimie Moléculaire, École Polytechnique, Institut Polytechnique de Paris, CNRS Route de Saclay 91128 Palaiseau cedex, France.
A cross-electrophilic coupling of benzyl sulfonium salts with alkyl halides forming Csp-Csp bonds is described by using a Co-based catalytic system. The activation of the stable Csp-S bond of benzyl sulfonium salts under mild reaction conditions leads to various functionalized alkyl derivatives. Preliminary mechanistic studies suggest the involvement of alkyl radicals formed from both alkyl halides and benzyl sulfoniums through a single electron transfer.
View Article and Find Full Text PDFNickel-Catalysed Cross-Electrophile Coupling of Benzyl Bromides and Sulfonium Salts towards the Synthesis of Dihydrostilbenes.
Chemistry
September 2022
Departamento de Química Orgánica (Módulo 1), Universidad Autónoma de Madrid, 28049, Madrid, Spain.
A nickel-catalysed reductive cross-coupling reaction between benzyl sulfonium salts and benzyl bromides is reported. Simple, stable and readily available sulfonium salts have shown their ability as leaving groups in cross-electrophile coupling, allowing the formation of challenging sp -sp carbon-carbon bonds, towards the synthesis of interesting dihydrostilbene derivatives. In addition, benzyl tosyl derivatives have been demonstrated to be suitable substrates for reductive cross-coupling by in-situ formation of the corresponding sulfonium salt.
View Article and Find Full Text PDFChemo-Enzymatic Modification of the 5' Cap To Study mRNAs.
Acc Chem Res
May 2022
Department of Chemistry and Pharmacy, Institute of Biochemistry Westfälische Wilhelms-Universität Münster, University of Münster, Corrensstrasse 36, 48149 Münster, Germany.
The central dogma of molecular biology hinges on messenger RNA (mRNA), which presents a blueprint of the genetic information encoded in the DNA and serves as a template for translation into proteins. In addition to its fundamental importance in basic research, this class of biomolecules has recently become the first approved Covid vaccine, underscoring its utility in medical applications.Eukaryotic mRNA is heavily processed, including the 5' cap as the primary hallmark.
View Article and Find Full Text PDFSynthesis of 6Benzo[]chromene Scaffolds from -Benzylated Phenols through a C-H Sulfenylation/Radical Cyclization Sequence.
Org Lett
March 2021
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr 2, 37077-Göttingen, Germany.
-Aryl dibenzothiophenium salts, obtained through a highly regioselective C-H sulfenylation of -benzyl-protected phenols, are used as precursors of 6-benzo[]chromenes. The reaction starts with a photocatalytically triggered single-electron transfer to the sulfonium salt, which promotes the formation of an aryl radical via selective mesolitic cleavage of the S-Ar bond. Mechanistic studies reveal that this initial radical species cyclizes following a kinetically favored 5-exo-trig pathway.
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!