56361-22-9Relevant academic research and scientific papers
Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants
Jeremias, Noah,Mohr, Lisa-Marie,Bach, Thorsten
supporting information, p. 5674 - 5678 (2021/08/03)
2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).
Vinyl sulfone synthesisviacopper-catalyzed three-component decarboxylative addition
An, Seunghwan,Lee, Sunwoo,Song, Kwang Ho
supporting information, p. 7827 - 7831 (2021/09/28)
The synthesis of vinyl sulfone derivativesviathe reaction of arylpropiolic acids, K2S2O5, and aryl boronic acids is reported. The CuBr2/1,10-phenanthroline catalytic system in the presence of acetic acid provide
An efficient and straightforward route to terminal vinyl sulfones via palladium-catalyzed Suzuki reactions of α-bromo ethenylsulfones
Fang, Yewen,Yuan, Meijuan,Zhang, Juncong,Zhang, Li,Jin, Xiaoping,Li, Ruifeng,Li, Jinjian
supporting information, p. 1460 - 1463 (2016/03/12)
A general and simple protocol for the synthesis of α-substituted alkenylsulfones has been developed firstly via palladium-catalyzed Suzuki reactions between α-bromo ethenylsulfones and organoborons. Using a catalyst composed of Pd(OAc)2 and SPhos, a variety of aryl, heteroaryl, and alkylboron reagents could efficiently couple with α-bromo ethenylsulfones under mild conditions. Moreover, it has been demonstrated for the first time that vinyl sulfones underwent smooth reduction by diimide generated from 2-nitrobenzenesulfonylhydrazide.
Electrosynthesis of (E)-Vinyl Sulfones Directly from Cinnamic Acids and Sodium Sulfinates via Decarboxylative Sulfono Functionalization
Qian, Peng,Bi, Meixiang,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
, p. 4876 - 4882 (2016/07/06)
A variety of (E)-vinyl sulfones were constructed directly from cinnamic acids and sodium sulfinates with high regioselectivity at room temperature by virtue of an electrocatalytic oxidation. A radical intermediate was detected, and the corresponding mecha
Phosphoric Acid-Mediated Synthesis of Vinyl Sulfones through Decarboxylative Coupling Reactions of Sodium Sulfinates with Phenylpropiolic Acids
Rong, Guangwei,Mao, Jincheng,Yan, Hong,Zheng, Yang,Zhang, Guoqi
, p. 7652 - 7657 (2015/08/18)
A novel phosphoric acid -mediated synthesis of vinyl sulfones through decarboxylative coupling reactions of sodium sulfinates with phenylpropiolic acids is described. This transformation is efficient and environmentally friendly.
Iodine-promoted decarboxylative C-S cross-coupling of cinnamic acids with sodium benzene sulfinates
Chen, Jie,Mao, Jincheng,Zheng, Yang,Liu, Defu,Rong, Guangwei,Yan, Hong,Zhang, Cheng,Shi, Daqing
, p. 5059 - 5063 (2015/06/25)
We have developed a practical example of metal-free iodine-promoted decarboxyltive couplings between cinnamic acids and sodium benzene sulfinates, which represents an effective synthesis of vinyl sulfones via C-S bond formation reaction.
Photoredox α-vinylation of α-amino acids and N -aryl amines
Noble, Adam,MacMillan, David W. C.
, p. 11602 - 11605 (2014/11/08)
A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.
Copper-catalyzed highly selective direct hydrosulfonylation of alkynes with arylsulfinic acids leading to vinyl sulfones
Wei, Wei,Li, Jinli,Yang, Daoshan,Wen, Jiangwei,Jiao, Yueting,You, Jinmao,Wang, Hua
, p. 1861 - 1864 (2014/03/21)
A novel Cu-catalyzed direct hydrosulfonylation of alkynes with arylsulfinic acids for the synthesis of (E)-vinyl sulfones has been realized under mild conditions with 100% atom efficiency. The present protocol provides an attractive approach to various vinyl sulfones in good to excellent yields, with the advantages of operation simplicity, atom economy, and high stereo- and regioselectivities.
Heck vinylations using vinyl sulfide, vinyl sulfoxide, vinyl sulfone, or vinyl sulfonate derivatives and aryl bromides catalyzed by a palladium complex derived from a tetraphosphine
Battace, Ahmed,Zair, Touriya,Doucet, Henri,Santelli, Maurice
, p. 3495 - 3505 (2008/02/10)
The adverse impact of sulfur compounds on catalytic performance is well known. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino) methyl]cyclopentane in combination with allylchloropalladium dimer affords an efficient catalyst for the Hec
Process for producing [2-(arylsulfonyl) ethenyl] benzene derivatives
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, (2008/06/13)
The present invention provides a safer and more efficient process for producing [2-(arylsulfonyl)ethenyl]benzene derivatives of the formula (3): wherein R1, R2, R3 and R4 are the same or different and each independently represent a hydrogen, fluorine, or chlorine atom, a lower alkyl group, or the like, and two adjacent R3 and R4 may bond each other at their terminals to form a ring, which the process is characterized in that a 2-(arylsulfonyl)ethanol of formula (1): wherein R1 and R2 are as defined above, and an acid anhydride are reacted in the presence of a base, and the reaction liquid obtained is supplied to a reaction with an aromatic halide of formula (2): wherein X represents a chlorine, bromine, or iodine atom, and R3 and R4 are the same as defined above, in the presence of a palladium catalyst and a base.
