- Electrochemical-In-Situ-Oxidative Sulfonylation of Phenols with Sulfinic Acids as an Access to Sulfonylated Hydroquinones
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The electrochemical in-situ oxidative sulfonylation of phenols with sulfinic acids access to sulfonylated hydroquinones has been developed. A series of sulfonylated hydroquinones were prepared under mild mediator-, catalyst- and exogenous-oxidant-free con
- Sun, Xue,Zhang, Fanjun,Yan, Kelu,Feng, Wenfeng,Sun, Xuejun,Yang, Jianjing,Wen, Jiangwei
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supporting information
p. 3485 - 3490
(2021/06/17)
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- One-pot access to sulfonylated naphthalenediols/hydroquinones from naphthols/phenols with sodium sulfinates in an aqueous medium
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A one-pot method towards sulfonylated hydroquinones/naphthalenediols in an aqueous medium has been developed with up to 97% yield. The whole reaction requiring no transition-metal catalysts could proceed smoothly with hypervalent iodine compounds as the oxidant. Both naphthols and phenols were viable with inexpensive and readily available sodium sulfinates as the sulfonylation reagents under an ambient atmosphere. This procedure is scalable, and the products could be easily obtained without column chromatography isolation. This journal is
- Meng, Lingxin,Zhang, Ruike,Guan, Yuqiu,Chen, Tian,Ding, Zhiqiang,Wang, Gongshu,Reheman, Aikebaier,Chen, Zhangpei,Hu, Jianshe
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p. 610 - 614
(2021/01/25)
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- Metal-free sulfonylation of quinones with sulfonyl hydrazides in water: Facile access to mono-sulfonylated hydroquinones
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This paper describes a simple and practical protocol for the direct synthesis of monosulfonylated hydroquinones through a transition-metal-free cross-coupling between quinones and sulfonyl hydrazides in water. The procedure tolerates a variety of quinones
- Li, Bin,Li, Yaqin,Yu, Linqian,Wu, Xiaoyu,Wei, Wanguo
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p. 2760 - 2765
(2017/04/14)
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- Preparation method for sulfonyl hydroquinone compound
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The invention belongs to the field of organic synthesis, and in particular, relates to a preparation method for a sulfonyl hydroquinone compound. According to the preparation method, a cheap and easily obtained quinone compound is used as a raw material, stable and easy-to-preserve sulfonyl hydrazide is used as a sulfonylation reagent, metal-free catalysis is adopted, reaction conditions are environmentally friendly, the preparation process is simplified, and the yield is increased.
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Paragraph 0062; 0063; 0064
(2017/04/29)
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- Hydroxysulfonylation of Quinones with Aryl(alkyl)sulfonyl Hydrazides for the Synthesis of 1,4-Dihydroxy-2-aryl(alkyl)sulfonylbenzenes
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β-Ketoacyl-ACP-synthase III (FabH) plays an important role in bacterial fatty-acid biosynthesis as an important condensing enzyme. 1,4-Dihydroxy-2-tosylnaphthalene and its analogues are potent inhibitors of FabH. Traditional methods for the synthesis of these compounds still suffer from some drawbacks. In this work, an efficient copper-catalyzed method for the hydroxysulfonylation of quinones with aryl(alkyl)sulfonyl hydrazides was developed for the direct synthesis of 1,4-dihydroxy-2-phenylsufonylbenzenes. A series of biologically useful FabH inhibitors were obtained in good yields under argon. Both aryl and alkyl substituents were well tolerated in the reaction.
- Li, Ping-Gui,Li, Yan-Chun,Zhu, Tao,Zou, Liang-Hua,Wu, Zhimeng
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supporting information
p. 6081 - 6084
(2017/11/14)
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- Green and mild laccase-catalyzed aerobic oxidative coupling of benzenediol derivatives with various sodium benzenesulfinates
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The oxidative coupling reaction between hydroquinone or catechols and various sodium benzenesulfinates was investigated using the laccase from Trametes versicolor, in the presence of O2in a phosphate buffer solution at room temperature to afford sulfonyl benzenediols in 75–95% yield.
- Habibi, Davood,Rahimi, Abdollah,Rostami, Amin,Moradi, Sirvan
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supporting information
p. 289 - 293
(2017/01/03)
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- Ammonium iodide-promoted unprecedented arylsulfonylation of quinone with sodium arylsulfinates
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A novel ammonium iodide-promoted arylsulfonylation of quinones with sodium arylsulfinates has been explored. This reaction proceeded smoothly through unique nucleophilic addition reaction and produced the arylsulfonylation products in moderate to good yields. The reactions proceeded efficiently over a broad range of substrates with good regioselectivity and functional group tolerance.
- Yuan, Jin-Wei,Liu, Shuai-Nan,Qu, Ling-Bo
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p. 6763 - 6772
(2017/10/26)
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- Ir-catalyzed C–S coupling of quinones with sulfonyl chloride
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Abstract: A concise, efficient method to sulfonyl quinones and sulfonyl-1,4-diols through Ir-catalyzed C–S coupling of quinones with sulfonyl chloride has been developed. Thus, this methodology proves its value as a versatile synthetic tool for a broad ra
- Wang, Long,Xie, Yi-Bi,Yang, Quan-Li,Liu, Ming-Guo,Zheng, Kai-Bo,Hu, Yu-lin,Huang, Nian-Yu
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p. 1797 - 1803
(2016/08/25)
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- Different strategies in electrochemical synthesis of new mono and di-substituted hydroquinone and benzoquinone
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Electrochemical syntheses of 2-indolyl-5-arylsulfonyl-p-benzoquinone derivatives were carried out in two successive oxidation steps. The first involves the oxidation of hydroquinone, 4-(piperazin-1-yl) phenol) and 1-(4-(4-hydroxyphenyl) piperazin-1-yl) et
- Nematollahi, Davood,Momeni, Shima,Khazalpour, Sadegh
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p. 310 - 318
(2015/02/02)
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- Synthesis of arylsulfonyl-quinones and arylsulfonyl-1,4-diols as FabH inhibitors: Pd-catalyzed direct C-sulfone formation by CS coupling of quinones with arylsulfonyl chloride
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The Pd-catalyzed direct C-sulfone formation by C-S coupling of quinones with arylsulfonyl chloride has been developed. This methodology provides an effective, convenient method for the synthesis of arylsulfonyl-quinones and arylsulfonyl-1,4-diols, which a
- Ge, Bingyang,Wang, Dawei,Dong, Weifu,Ma, Piming,Li, Yongliang,Ding, Yuqiang
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supporting information
p. 5443 - 5446
(2014/12/11)
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- Synthesis and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors
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A series of analogs of 2-tosylnaphthalene-1,4-diol were prepared and were found to be potent 10-20 nM reversible inhibitors of the Escherichia coli FabH enzyme. The inhibitors were also effective but to a lesser degree (30 nM-5 μM), against the Mycobacter
- Alhamadsheh, Mamoun M.,Waters, Norman C.,Sachdeva, Sarbjot,Lee, Patricia,Reynolds, Kevin A.
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supporting information; experimental part
p. 6402 - 6405
(2009/09/30)
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- Ionic liquids-promoted addition of arylsulfinic acids to p-quinones: A green synthesis of diaryl sulfones
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Arylsulfinic acids undergo smooth conjugate addition to p-quinones in air- and moisture-stable second generation room temperature ionic liquid [bmim]BF4 under mild conditions to produce the corresponding arylsulfonylhydroquinones in excellent yields with high selectivity. In this reaction, ionic liquid plays the dual role as the solvent and the catalyst. The quinones show enhanced reactivity in ionic liquid thereby reducing the reaction times and improving the yields significantly. The presence of ionic liquids helps to avoid the use of either acid or base catalysts for this conversion. The recovered ionic liquid was reused for four to five times with consistent activity.
- Yadav,Reddy,Swamy,Ramireddy
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p. 1849 - 1853
(2007/10/03)
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