39654-06-3Relevant academic research and scientific papers
Solvent-Driven Mono- and Bis-sulfenylation of (E)-β-Iodovinyl Sulfones with Thiols for Flexible Synthesis of 1,2-Thiosulfonylalkenes and 1,2-Dithioalkenes
Reddy, Raju Jannapu,Kumari, Arram Haritha,Sharadha, Nunavath,Krishna, Gamidi Rama
, p. 3934 - 3951 (2022/03/16)
The nature of solvent is a key factor for stereoselective mono- and bis-thiolation of (E)-β-iodovinyl sulfones with thiols under basic conditions. A novel and unprecedented vicinal bisthiolation of (E)-β-iodovinyl sulfones with thiols under the influence of K2CO3/DMSO at room temperature for quick assembly of (E)-1,2-dithio-1-alkenes is presented. Solvent-induced stereoselective monosulfenylation of (E)-β-iodovinyl sulfones with thiols has also been established for the synthesis of both (E)- and (Z)-1,2-thiosulfonylethenes in MeCN and MeOH, respectively. Moreover, K2CO3-mediated desulfonylative-sulfenylation of (Z)-1,2-thiosulfonylethenes with thiols in DMSO furnished unsymmetrical (Z)-1,2-dithio-1-alkenes for the first time. The solvent-dependent versatile reactivity of (E)-β-iodovinyl sulfones has been successfully explored to provide a set of (E)-/(Z)-1,2-dithio-1-alkenes and (E)-/(Z)-1,2-thiosulfonyl-1-alkenes in good to high yields with excellent stereoselectivities. Notably, this operationally simple process utilizes a broad substrate scope with good functional group tolerance and compatibility. The efficacy of the process has been proven for gram-scale reactions, and plausible mechanistic models are outlined on the basis of experimental results and control experiments.
Palladium-catalyzed bisthiolation of terminal alkynes for the assembly of diverse (Z)-1,2-bis(arylthio)alkene derivatives
Chen, Zi-Shen,Du, Yu-Long,He, Dan,Lai, Yin-Long,Li, Jianxiao,Yan, Shaoxi,Zhou, Li-Zhen
, p. 28447 - 28451 (2021/09/22)
An efficient and straightforward palladium-catalyzed three-component cascade bisthiolation of terminal alkynes and arylhydrazines with sodium thiosulfate (Na2S2O3) as the sulfur source for the assembly of functionalized (Z)-1,2-bis(arylthio)alkene derivatives is described. Using 0.5 mol% IPr-Pd-Im-Cl2as the catalyst, a wide range of terminal alkynes and arylhydrazines are well tolerated, thus producing the desired products in good yields with good functional group tolerance and excellent regioselectivity. Moreover, this protocol could be readily scaled up, showing potential applications in organic synthesis and material science.
Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism
Liu, Bin,Alegre-Requena, Juan V.,Paton, Robert S.,Miyake, Garret M.
supporting information, p. 2386 - 2394 (2020/02/05)
1,2-Dithio-1-alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2-dithio-1-alkenes often demand transition metal
Palladium-Catalyzed Regioselective Three-Component Cascade Bisthiolation of Terminal Alkynes
Li, Jianxiao,Li, Can,Ouyang, Lu,Li, Chunsheng,Yang, Shaorong,Wu, Wanqing,Jiang, Huanfeng
, p. 1138 - 1150 (2018/02/06)
An efficient and novel NHC(N-heterocyclic carbene)-palladium-catalyzed three-component cascade bisthiolation of terminal alkynes, K2S (potassium sulfide) and diaryliodonium salts for the assembly of functionalized (Z)-1,2-bis(arylthio)alkene derivatives has been accomplished for the first time. This unique observation features a broad substrate scope, excellent functional-group tolerance, and high regioselectivity. Especially, an arylthiolate anion from diaryliodonium salts and potassium sulfide was proposed as the key intermediate in the catalytic cycle. (Figure presented.).
Nickel-Catalyzed Regioselective Cleavage of Csp2-S Bonds: Method for the Synthesis of Tri- and Tetrasubstituted Alkenes
Chen, Jinyang,Chen, Sihai,Xu, Xinhua,Tang, Zhi,Au, Chak-Tong,Qiu, Renhua
, p. 3246 - 3255 (2016/05/19)
We describe here an efficient route for the synthesis of (Z)-vinylic sulfides 3 via the highly regio- and stereoselective coupling of (Z)-1,2-bis(aryl(alkyl)thio)alkenes and Grignard reagents over a Ni catalyst under mild conditions. (Z)-Vinylic sulfides 3 are important intermediates in the synthesis of tri- and tetrasubstituted alkenes that are important construction blocks for drugs and natural products. The directing organosulfur groups (SR) can be converted to diaryl(alkyl) disulfides (RSSR) using H2O2 as oxidant, hence avoiding the waste of sulfur resources. The protocol provides a general method that is highly regio- and stereoselective for the synthesis of a diversity of tri- and tetrasubstituted alkenes.
Addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex
Li, Jianying,Liu, Jun,Cai, Mingzhong
experimental part, p. 616 - 618 (2011/02/26)
A variety of (Z)-1,2-bis(arylthio)-substituted alkenes have been conveniently synthesised in high yields by the stereoselective addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex. Th
"β-cis-SAr effect" on decarbonylation from α,β-unsaturated acyl and aroyl complexes
Kato, Tomohiro,Kuniyasu, Hitoshi,Kajiura, Takamichi,Minami, Yasunori,Ohtaka, Atsushi,Kinomoto, Masanori,Terao, Jun,Kurosawa, Hideo,Kambe, Nobuaki
, p. 868 - 870 (2008/02/08)
Lone pair of heteroatom located at the β-cis position in α,β-unsaturated acyl and aroyl group 10 metal complexes dramatically facilitated the stoichiometric and catalytic decarbonylation reactions. The Royal Society of Chemistry 2006.
