108918-97-4Relevant academic research and scientific papers
Solid-phase synthesis of β-keto sulfones
Qian, Hao,Huang, Xian
, p. 1934 - 1936 (2006)
A novel method for the preparation of β-keto-sulfones through the use of organoselenium reagents in the solid phase by polystyrene-supported benzeneselenosulfonate or tolueneseleno-sulfonate with acetylenes has been developed. Georg Thieme Verlag Stuttgart.
Synthesis of (E)-β-Selenovinyl Sulfones through a Multicomponent Regio- and Stereospecific Selenosulfonation of Alkynes with Insertion of Sulfur Dioxide
Sun, Kai,Shi, Zuodong,Liu, Zhenhua,Luan, Baixue,Zhu, Jiali,Xue, Yanru
, p. 6687 - 6690 (2018)
A novel and practical method for the selenosulfonation of alkynes with the insertion of sulfur dioxide has been developed. A series of β-(seleno)vinyl sulfones with high levels of regio- and stereoselectivity have been prepared. The key features of this reaction include a broad substrate scope, excellent functional-group tolerance, and amenability to scale-up synthesis. A plausible radical mechanism is proposed to illustrate this reaction.
Copper-Catalyzed Three Component Regio- and Stereospecific Selenosulfonation of Alkynes: Synthesis of (E)-β-Selenovinyl Sulfones
Liu, Yang,Zheng, Guangfan,Zhang, Qian,Li, Yan
, p. 2269 - 2275 (2017/02/26)
A copper-catalyzed highly regio- and stereospecific selenosulfonation of alkynes with arylsulfonohydrazides and diphenyl diselenide has been developed. This novel three component reaction proceeds under very mild conditions and with a broad scope of substrates, providing a wide range of (E)-β-selenovinyl sulfones in good to excellent yields.
Metal-free selenosulfonylation of alkynes: Rapid access to β-(seleno)vinyl sulfones via a cationic-species-induced pathway
Sun, Kai,Wang, Xin,Fu, Fangfang,Zhang, Chong,Chen, Yao,Liu, Lin
, p. 1490 - 1493 (2017/05/10)
A novel and convenient method has been developed for the 1,2-selenosulfonylation of alkynes under metal-free conditions. The reaction avoids the need for the pre-prepared Se-S reagents, providing facile access to a series of β-(seleno)vinyl sulfones with
1,3-Dipolar cycloadditions of acetylenic sulfones in solution and on solid supports
Gao, Detian,Zhai, Huimin,Parvez, Masood,Back, Thomas G.
, p. 8057 - 8068 (2008/12/22)
(Chemical Equation Presented) Several representative acetylenic sulfones were immobilized on a polymer support derived from Merrifield resin by means of ester linkers that were used to couple free carboxylic acid groups on the solid support with benzylic hydroxyl functions on the arylsulfonyl moieties of the acetylenes. Several examples of reversed ester linkers, using Merrifield resin directly, were also successfully prepared. The 1,3-dipolar cycloadditions of the solid-supported acetylenic sulfones were investigated with a series of 1,3-dipoles, including benzyl azide, ethyl diazoacetate, diazomethane, as well as representative nitrile oxides, nitrile imines, nitrile ylides, nitrones, azomethine imines, azomethine ylides, munchnones, and sydnones. In general, analogous cycloadditions were also performed with acetylenic sulfones in solution phase for comparison. The cycloadditions typically afforded good to excellent yields of the desired products in both solution and solid phase, although the latter reactions sometimes required more vigorous conditions. Except in the case of benzyl azide and diazo compounds, where mixtures of regioisomers were obtained, the other 1,3-dipoles reacted with high regioselectivity and afforded essentially unique regioisomers. Cleavage of the products from the resin was smoothly effected by alkaline hydrolysis, while several attempts at reductive desulfonylation with sodium amalgam or samarium diiodide-HMPA resulted in N-O or C-O scission, in addition to cleavage from the polymer. The method provides access to a number of important classes of heterocycles, including variously substituted and functionalized triazoles, pyrazoles, 1,2-oxazoles, pyrroles, as well as their dihydro and bicyclic analogues. The success of the cycloadditions on polymer supports paves the way to future investigations of sequential transformations leading to libraries of useful heterocycles.
Substitution Reactions of Carbon Nucleophiles with β-(Phenylseleno)vinyl Sulfone Se Oxides
Back, Thomas G.,Krishna, M. Vijaya
, p. 4265 - 4269 (2007/10/02)
Selenoxides 2, obtained from the selenosulfonation and peracid oxidation of acetylenes, reacted with various nucleophiles to afford the products of overall substitution of the PhSeO moiety.Anions of dimethyl malonate, ethyl acetoacetate, malononitrile, 1-
