A convenient and base-free three-component reaction has been developed for the synthesis of S-alkyl substituted isothioureas from cyclic sulfonium salts, isothiocyanates, and amines. This protocol provides an alternative avenue to access a series of S-alkyl substituted isothioureas in moderate to good yields through ring-opening reaction of aryl, alkenyl and alkynyl sulfonium salts. The present strategy features operational simplicity, good functional group tolerance, gram-scale synthesis and high reaction efficiency.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/chem.202403990 | DOI Listing |
Org 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.
View Article and Find Full Text PDFOrg Lett
December 2024
Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, P. R. China.
Herein, we report a novel and practical strategy for alkyl sulfonium salts mediating radical thiocyanohydroxylation of alkenes. This reaction features metal-free and mild conditions, generation of noncarbon radicals from the readily available alkyl sulfonium salts, easy handling, and excellent functional group compatibility. A diverse range of activated and unactivated alkenes worked well to deliver various β-thiocyanato alcohols.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!