126745-33-3Relevant academic research and scientific papers
Aerobic Copper-Catalyzed Synthesis of (E)-Vinyl Sulfones by Direct C-S Bond Oxidative Coupling
Liang, Xiao,Xiong, Mingteng,Zhu, Heping,Shen, Kexin,Pan, Yuanjiang
, p. 11210 - 11218 (2019/09/12)
Copper-catalyzed aerobic oxidative C-S bond coupling reaction between thiophenols and aryl-substituted alkenes for (E)-vinyl sulfones synthesis is reported here. With air utilized as a green oxidant, this transformation not only produces various vinyl sulfones in moderate to good yields but also possesses a simple and ecofriendly system. To clarify the mechanism, kinetic experiments has been investigated.
Sulfones as Synthetic Linchpins: Transition-Metal-Free sp3–sp2 and sp2–sp2 Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds
Trost, Barry M.,Kalnmals, Christopher A.
, p. 9066 - 9074 (2018/06/29)
A valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin is reported. Although the bis(phenylsulfonyl)methyl group is typically introduced as an sp3-carbon nucleophile, it is demonstrated that it can also function as an effective sp2-carbon electrophile in the presence of organolithium nucleophiles. Alkyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross-couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at ?78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable synthetic linchpin, which can undergo two C?C bond-forming processes as an sp3-nucleophile, followed by a third C?C bond-forming reaction as an effective sp2-electrophile. This discovery significantly enhances the utility of this ubiquitous, but underutilized, linker group.
E -Selective synthesis of vinyl sulfones via silver-catalyzed sulfonylation of styrenes
Gui, Qingwen,Han, Kang,Liu, Zhuoliang,Su, Zhaohong,He, Xiaoli,Jiang, Hongmei,Tian, Bufan,Li, Yangyan
supporting information, p. 5748 - 5751 (2018/08/21)
An efficient and highly E-selective protocol for the synthesis of vinyl sulfones is described. This simple protocol demonstrates the first synthesis of vinyl sulfones via a silver-catalyzed C-S bond coupling reaction. In addition, the success of the reaction was found to be critically dependent on the use of TEMPO as the additive.
Photocatalytic Oxidation of Sulfinates to Vinyl Sulfones with Cyanamide-Functionalised Carbon Nitride
Meyer, Andreas Uwe,Lau, Vincent Wing-hei,K?nig, Burkhard,Lotsch, Bettina V.
, p. 2179 - 2185 (2017/04/24)
The cyanamide-functionalised carbon nitride (NCN-CNx) can be employed as a photo-redox catalyst for the light-induced sulfonylation of alkenes with sulfinate salts, attaining product yields twice those obtained with the non-functionalised count
Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates
Meyer, Andreas Uwe,J?ger, Stefanie,Prasad Hari, Durga,K?nig, Burkhard
, p. 2050 - 2054 (2015/06/23)
Visible light and eosin Y catalyze the synthesis of vinyl sulfones from aryl sulfinates and alkenes by a photoredox process. The reaction scope is broad in aryl sulfinates and alkenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable vinyl sulfones.
Aromatization of Tetrahydrocyclopropanaphthalenes: an Alternative Synthesis of 1H-Cyclopropanaphthalene
Mueller, Paul,Bernardinelli, Gerald,Thi, Huong Can Godoy-Nguyen
, p. 1627 - 1638 (2007/10/02)
1H-Cyclopropanaphthalene (1a) is accessible via reduction of the dichloro compound 1c with LiAlH4/AlCl3.Several derivatives of tetrahydrocyclopropanaphthalene were synthesized.However, contrary to their 1,1-dihalogeno analogues, they afforded no cyc
