81763-76-0Relevant academic research and scientific papers
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
supporting information, p. 6687 - 6690 (2018/11/21)
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.
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
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.
Selenosulfonation of Acetylenes: Preparation of Novel β-(Phenylseleno)vinyl Sulfones and Their Conversion to Acetylenic and β-Functionalized Sulfones
Back, Thomas G.,Collins, Scott,Kerr, Russell G.
, p. 3077 - 3084 (2007/10/02)
The 1,2-additions of Se-phenyl p-tolueneselenosulfonate (1) to acetylenes under mild conditions afford β-(phenylseleno)vinyl sulfones 3, generally in high yields.The reaction is highly regioselective (anti-Markovnikov) and stereoselective (anti) and proceeds via a free-radical chain mechanism initiated by the thermolysis of the selenosulfonate.The oxidation of β-(phenylseleno)vinyl sulfones with m-chloroperbenzoic acid generates the corresponding selenoxides 4, which undergo syn or base-catalyzed elimination to furnish acetylenic sulfones 5.Base-catalyzed alcoholyses of selenoxides 4 in methanol or ethylene glycol produce β-keto sulfone ketals 8 or 10, respectively.Free β-keto sulfones 11 are formed by the acid-catalyzed hydrolysis of the corresponding β-(phenylseleno)vinyl sulfones 3.
SELENOSULFONATION OF ACETYLENES. PREPARATION OF NOVEL β-(PHENYLSELENO)VINYL SULFONES
Back, Thomas G.,Collins, Scott
, p. 5111 - 5114 (2007/10/02)
Se-Phenyl p-tolueneselenosulfonate (1) undergoes thermal addition to acetylenes to afford β-(phenylseleno)vinyl sulfone adducts 2 in a stereo- and regioselective fashion.
