56069-43-3Relevant academic research and scientific papers
Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones
Chawla, Ruchi,Jaiswal, Shefali,Dutta,Yadav, Lal Dhar S.
supporting information, (2020/04/15)
A photocatalyst-free visible light mediated decarboxylative sulfono functionalization protocol has been explored for the synthesis of (E)-vinyl sulfones from cinnamic acids and bench-stable arylazo sulfones. The latter have been utilized as sulfonyl radic
Dual ligand-promoted palladium-catalyzed nondirected C-H alkenylation of aryl ethers
Fu, Manlin,Liu, Jiang,Wang, Lei,Yin, Biao,Zhu, Qing
supporting information, p. 3293 - 3296 (2020/04/02)
Direct C-H functionalization of aryl ethers remains challenging owing to their low reactivity and selectivity. Herein, a novel strategy for nondirected C-H alkenylation of aryl ethers promoted by a dual ligand catalyst was demonstrated. This catalytic system readily achieved the highly efficient alkenylation of alkyl aryl ethers (anisole, phenetole, n-propyl phenyl ether, n-butyl phenyl ether and benzyl phenyl ether), cyclic aryl ethers (1,4-benzodioxan, 2,3-dihydrobenzofuran, dibenzofuran), and diphenyl oxides. Moreover, the proposed methodology was successfully employed for the late-stage modification of complex drugs containing the aryl ether motif. Interestingly, the compounds developed herein displayed fluorescent properties, which would facilitate their biological applications.
Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols with Sulfones: A Tool to Access Highly Substituted Vinyl Sulfones
Barman, Milan K.,Maji, Biplab,Waiba, Satyadeep
, p. 973 - 982 (2021/08/24)
The development of first-row-transition-metal catalysts that can match with the reactivities of the noble metals is considered to be challenging yet very much a desirable goal in homogeneous catalysis. It has become even more fascinating to develop processes where these metals show a unique reactivity and selectivity than their higher congeners. Herein, we report on the catalytic activity of a pincer complex of the abundant earth metal manganese for an unprecedented acceptorless dehydrogenative coupling of alkyl sulfones with alcohols. Thus, highly functionalized vinyl sulfones were obtained in moderate to good yields. Both benzylic and aliphatic alcohols could be utilized, and several functional groups including bromides and iodides are tolerated under the reaction conditions. The reaction is environmentally benign, producing dihydrogen and water as byproducts. Preliminary mechanistic experiments involving kinetic, deuterium-labeling, and NMR experiments were performed.
Stereoselective Synthesis of Alkenyl Silanes, Sulfones, Phosphine Oxides, and Nitroolefins by Radical C-S Bond Cleavage of Arylalkenyl Sulfides
Lin, Ya-mei,Lu, Guo-ping,Wang, Rong-kang,Yi, Wen-bin
, p. 1100 - 1103 (2017/03/15)
A radical-mediated approach has been introduced for the C-S bond activation of arylalkenyl sulfides. The protocol provides an efficient approach for the generation of various alkenes including alkenyl silanes, sulfones, phosphine oxides, and nitroolefins. In most cases, these radical substitutions are performed under metal-free conditions with stereospecificity.
Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism
Meyer, Andreas Uwe,Straková, Karolína,Slanina, Tomá?,K?nig, Burkhard
supporting information, p. 8694 - 8699 (2016/07/07)
Alkyl- and aryl vinyl sulfones were obtained by eosin Y (EY)-mediated visible-light photooxidation of sulfinate salts and the reaction of the resulting S-centered radicals with alkenes. Optimized reaction conditions, the sulfinate and alkene scope, and X-ray structural analyses of several reaction products are provided. A detailed spectroscopic study explains the reaction mechanism, which proceeds through the EY radical cation as key intermediate oxidizing the sulfinate salts.
CuSO4?·5H2O-H-phosphonate-catalyzed intermolecular C-S bond formation: Synthesis of (E)-vinyl alkylsulfones from alkynes and DMSO
Chen, Jian-Yu,Chen, Xiao-Lan,Li, Xu,Qu, Ling-Bo,Zhang, Qing,Duan, Li-Kun,Xia, Ying-Ya,Chen, Xin,Sun, Kai,Liu, Zhi-Dong,Zhao, Yu-Fen
supporting information, p. 314 - 319 (2015/02/02)
A CuSO4?·5H2O-H-phosphonate-catalyzed synthesis of (E)-vinyl alkylsulfones from alkynes and widely available DMSO was developed. The present protocol provides an alternative approach to various vinyl sulfones, with the advantages of cheap catalysts, readily available starting materials, operational simplicity and high stereo- and regioselectivity.
Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones
Gao, Xiaofang,Pan, Xiaojun,Gao, Jian,Huang, Huawen,Yuan, Gaoqing,Li, Yingwei
supporting information, p. 210 - 212 (2015/01/09)
A novel ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones is described. The process proceeded smoothly under metal-free conditions with high stereoselectivity and good functional group toler
CuI/L-proline potassium salt catalysed synthesis of vinyl sulfones via coupling reaction of vinyl bromides with sulfinic acid salts in ionic liquid
Bao, Weiliang,Wang, Congna
, p. 396 - 397 (2007/10/03)
Catalysed by CuI/L-proline potassium salt, which serves as both base and ligand, the coupling reaction of vinyl bromides with sulfinic acid salts occurs at 110°C in ionic liquid to give the corresponding vinyl sulfones in good yields.
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
SYNTHESIS AND ALKYLATION OF VINYLSULFINIC ACIDS VIA FLUORIDE CLEAVAGE OF β-TRIMETHYLSILYLETHYL VINYL SULFONES
Palmer, James T.,Fuchs, P. L.
, p. 233 - 246 (2007/10/02)
A new method for the synthesis of vinylsulfinic acids from aldehydes is described.The homologated vinyl (trimethylsilylethyl)sulfones were synthesized from the corresponding aldehydes by means of the phosphonium salt derived from the chloromethylsulfide o
