This minireview aims to cover the developments over the past two decades in the chemistry of sulfonium salts. Specifically, insight is provided into the synthetic strategies available for the preparation of these compounds, the different reactivity patterns that are expected depending on their structural features or the reaction conditions applied, and the diversity of organic scaffolds that can thereby be synthesized. Additionally, the pros and cons derived from the use of sulfonium salts are presented and critically compared, when possible, in relation to reagents not based on sulfur but depicting similar reactivity.
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http://dx.doi.org/10.1002/ejic.202000249 | DOI Listing |
Org Lett
January 2025
Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.
Here, we present a three-component successive radical addition strategy for the preparation of complex noncanonical α-amino acids from easily available glycine derivatives, alkenes, and aryl sulfonium salts via a copper-catalyzed photoredox-neutral catalytic cycle. The utility of this method is further demonstrated by its application in late-stage site-selective modifications of glycine residues in short peptides. It is worth noting that only 1 mol % copper catalyst is required in this reaction, demonstrating high catalytic efficiency.
View Article and Find Full Text PDFOrg Lett
December 2024
Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, School of Pharmacy, Zunyi Medical University, Zunyi 563003, China.
We report an efficient, metal-free method for late-stage rapid [F]trifluoromethyl radiolabeling of terminal alkenes at room temperature. Utilizing 3,3-difluoroallyl sulfonium salts as precursors, the process achieves high radiochemical yields (up to 94 ± 2%) in just 30 s, with excellent functional group tolerance. This method offers a simplified and efficient pathway to produce [F]trifluoromethylated terminal alkene compounds, enabling their application in PET imaging and expanding the chemical space for drug discovery.
View Article and Find Full Text PDFChemistry
December 2024
School of Chemical & Environmental Engineering, Yancheng Teachers University, Yancheng, Jiangsu, 224007, China.
Chem Rec
December 2024
Department of Chemistry, Universidade Federal de Minas Gerais (UFMG), 31.270-901, Belo Horizonte, MG, Brazil.
Alkylation reactions and their products are considered crucial in various contexts. Synthetically, the alkylation of a nucleophile is usually promoted using hazardous alkyl halides. Here, we aim to highlight the potential of pnictogen (ammonium or phosphonium) and chalcogen salts (sulfonium, selenonium, and telluronium) to function as alkylating agents.
View Article and Find Full Text PDFNat Commun
November 2024
College of Chemistry, Zhengzhou University, Zhengzhou, 450001, China.
Aryl thianthrenium salts are valuable in photocatalysis but traditionally require external electron donors for activation. This study introduces an energy transfer (EnT) strategy for the activation of aryl thianthrenium salts using 2,3,4,5,6-penta(carbazol-9-yl)benzonitrile (5CzBN) as a metal-free photocatalyst, eliminating the need for external donors. Utilizing this EnT approach, we achieve C-H deuteration of arenes under visible light with CDCl as a deuterium source to synthesize various deuterated aromatic compounds, including important natural products and pharmaceuticals.
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