An efficient and practical method for synthesizing vinyl phosphorothioates has been demonstrated through a visible-light-induced three-component reaction of alkenyl sulfonium salts, S, and -phosphonates. This method facilitates the synthesis of a diverse range of vinyl phosphorothioates with a wide substrate scope and functional group tolerance. Preliminary mechanistic studies suggest that the reaction involves a phosphorothioate radical-triggered process.
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Visible-Light-Induced Phosphorothioation of Alkenyl Sulfonium Salts with S and -Phosphonates.
J Org Chem
February 2025
Key Laboratory of Comprehensive Utilization of Advantage Plants Resources of Southern Hunan, College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China.
An efficient and practical method for synthesizing vinyl phosphorothioates has been demonstrated through a visible-light-induced three-component reaction of alkenyl sulfonium salts, S, and -phosphonates. This method facilitates the synthesis of a diverse range of vinyl phosphorothioates with a wide substrate scope and functional group tolerance. Preliminary mechanistic studies suggest that the reaction involves a phosphorothioate radical-triggered process.
View Article and Find Full Text PDFBase-Free Synthesis of S-Alkyl Isothioureas Through Ring-Opening Reaction of Sulfonium Salts with Isothiocyanates and Amines.
Chemistry
February 2025
School of Chemical & Environmental Engineering, Yancheng Teachers University, Yancheng, Jiangsu, 224007, China.
Article Synopsis
- - A new method for creating S-alkyl substituted isothioureas is introduced, using cyclic sulfonium salts, isothiocyanates, and amines in a simple three-component reaction.
- - This method allows for the production of these compounds through the ring-opening of various sulfonium salts, with yields ranging from moderate to good.
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Incorporating a sulfonyl group into parent molecules has been shown to effectively improve their synthetic applications and bioactivities. In this study, we present a straightforward and practical approach for the ring-opening reaction of alkenyl-aryl sulfonium salts with sodium sulfinates to produce a range of sulfur-containing alkyl sulfones. This method offers the benefits of mild reaction conditions, easily accessible raw materials, wide substrate applicability, good functional group compatibility, and operational simplicity.
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Mechanistic investigation of the gold-catalyzed oxidative reactions of thioalkynes with quinoline N-oxides was performed using density functional theory (DFT) calculations. For the oxidative rearrangement of thioalkynes with quinoline N-oxide to yield the same products, the C-oxidation of thioalkynes was predicted to be competitive with C-oxidation, with the C-oxidative process slightly more favorable. However, for the oxidative alkenylation of propargyl aryl thioethers with quinoline N-oxides, the C-oxidation of thioether by quinoline N-oxide generated the product 3-hydroxy-1-alkylidene phenylthiopropan-2-one.
View Article and Find Full Text PDFDithiolation of Alkenyl Sulfonium Salts with Arylthiols to Access 1,2-Dithioalkanes.
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College of Materials, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, Zhejiang 311121, China.
A dithiolation of alkenyl sulfonium salts with arylthiols is described, affording a series of 1,2-dithioalkanes in high yields. This protocol features mild and catalyst-free conditions and involves the formation of two C-S bonds sequentially via the regioselective addition of an arylthiol to the unsaturated C═C bonds, followed by the attack of another arylthiol to form 1,2-dithioalkanes exclusively.
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