68819-94-3Relevant academic research and scientific papers
Unusual Application for Phosphonium Salts and Phosphoranes: Synthesis of Chalcogenides
Moura, Igor M. R.,Tranquilino, Arisson,Sátiro, Barbara G.,Silva, Ricardo O.,De Oliveira-Silva, Diogo,Oliveira, Roberta A.,Menezes, Paulo H.
, p. 5954 - 5964 (2021/05/04)
A novel strategy for the synthesis of sulfides and selenides from phosphonium salts and thio- or selenesulfonates, commercially available compounds, is described. When phosphoranes were used in the reaction, different products were obtained. The methodology does not require the use of metals, reactive species, or anhydrous conditions to be performed.
Visible-light-driven radical 1,3-addition of selenosulfonates to vinyldiazo compounds
Li, Weiyu,Zhou, Lei
, p. 6652 - 6658 (2021/09/10)
Herein, we report a visible-light-driven radical 1,3-selenosulfonylation of vinyldiazo compounds with selenosulfonates, providing various γ-seleno allylic sulfones in good yields. This photochemical reaction was carried out at room temperature in an open flask using ethyl acetate as the solvent without any photocatalysts or additives. The control experiments corroborated that the 1,3-addition proceeded via a radical-chain propagation process. The synthetic applications of the resulting products were demonstrated by deselenization, reduction, bromination and allylation.
Alkene: Versus alkyne reactivity in unactivated 1,6-enynes: Regio-And chemoselective radical cyclization with chalcogens under metal-And oxidant-free conditions
Kudale, Vishal Suresh,Li, Jing,Mutra, Mohana Reddy,Tsai, Wu-Hsun,Wang, Jeh-Jeng
supporting information, p. 2288 - 2300 (2020/04/21)
Herein, we have developed metal and oxidant-free visible light-promoted alkene vs. alkyne regio-And chemoselective radical cascade cyclization of electronically unbiased 1,6-enynes with chalcogens to synthesize substituted pyrrolidines bearing chalcogens. The reaction generated three new bonds, namely, C-SO2, C-C, and C-Se under extremely mild conditions. Furthermore, we achieved regio-And chemoselective mono-addition of aromatic thiophenols with unactivated 1,6-enynes. The key features of this protocol are broad substrate scope, environment-friendly conditions, operational simplicity, atom economy, and amenability to gram-scale synthesis. The mechanistic studies corroborate that the reaction proceeds via a radical pathway.
Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium
Chen, Zhili,Hu, Fangli,Huang, Shengli,Zhao, Zhengxing,Mao, Hui,Qin, Wenling
, p. 8100 - 8111 (2019/06/17)
Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.
Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene: Ortho -quinone methide (VQM)
Huang, Shengli,Chen, Zhili,Mao, Hui,Hu, Fangli,Li, Dongmei,Tan, Yu,Yang, Fengqing,Qin, Wenling
supporting information, p. 1121 - 1129 (2019/02/07)
A metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM) was described herein. The reaction was conducted under mild conditions without any catalysts or additives. Preliminary mechanism studies revealed that the formation of VQM was the key for this alkyne di-functionalization reaction. The reaction could be applied in the enantioselective asymmetric synthesis of axially chiral styrene. Furthermore, the selenosulfonylation adducts can be transformed into useful naphtho[2,1-b]furan and benzofuran scaffolds.
Visible light-induced co- or cu-catalyzed selenosulfonylation of alkynes: Synthesis of β-(seleno)vinyl sulfones
Ji, Shun-Jun,Wang, Shun-Yi,Xu, Pei,Zhang, Rong
, (2019/10/08)
A visible light-induced Co- or Cu-catalyzed selenosulfonylation of alkynes for the synthesis of β-(seleno)vinyl sulfones is demonstrated. This method utilizes a low-cost cobalt salt or metal copper as the catalysts. The reaction goes through a photoinduced free radical addition of selenosulfonates to alkynes for the 1,2-selenosulfonylation of alkynes under mild conditions.
Electrochemical Oxidative Cross-Coupling Reaction to Access Unsymmetrical Thiosulfonates and Selenosulfonates
Zhang, Xiaofeng,Cui, Ting,Zhang, Yanghao,Gu, Weijin,Liu, Ping,Sun, Peipei
, p. 2014 - 2019 (2019/03/26)
The electrochemical oxidative cross-dehydrogenative coupling of arylsulfinic acids with thiophenols was achieved via a radical process. A wide range of arylsulfinic acids and substituted thiophenols were found to be tolerated, providing unsymmetrical thio
Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethyl-silane: A general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer
Ma, Xiaoshen,Herzon, Seth B.
supporting information, p. 2259 - 2265 (2018/09/14)
We show that cobalt bis(acetylacetonate) [Co(acac)2], tert-butyl hydroperoxide (TBHP), and triethylsilane (Et3SiH) constitute an inexpensive, general, and practical reagent combination to initiate a broad range of Markovnikov-selective alkene hydrofunctionalization reactions. These transformations are believed to proceed by cobalt-mediated hydrogen atom transfer (HAT) to the alkene substrate, followed by interception of the resulting alkyl radical intermediate with a SOMOphile. In addition, we report the first reductive couplings of unactivated alkenes and aryldiazonium salts by an HAT pathway. The simplicity and generality of the Co(acac)2–TBHP–Et3SiH reagent combination suggests it as a useful starting point to develop HAT reactions in complex settings.
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 (2018/11/21)
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.
Oxidative coupling of dichalcogenides with sodium sulfinates via copper-catalyzed cleavage of s-s and se-se bonds
Taniguchi, Nobukazu
, p. 1764 - 1770 (2015/02/19)
A copper-catalyzed sulfonylation of disulfides was achieved using sodium sulfinates in air. The reaction formed various sulfur-sulfone bonds efficiently and afforded thiosulfonates in good yields. Selenosulfonates could also be prepared with this procedure. Furthermore, both chalcogenide groups on the dichalcogenides were available in these reactions.
