One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide

Monika Horvat; Gregor Kodri?; Marjan Jereb; Jernej Iskra

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One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide

机译：三氟甲基芳基三氟甲基芳基聚乙烯化合物与过氧化氢氧化的一个罐合成三氟甲基亚砜

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Hydrogen peroxide was used for oxidation of various aryl trifluoromethyl sulfides. Trifluoroacetic acid was used as an activating solvent that enables non-catalyzed oxidation and increases selectivity for sulfoxide formation. As shown by oxidation of thianthrene TFA enhances electrophilic character of the oxidant and further oxidation of sulfoxide group is blocked. We have joined trifluoromethylthiolation of arenes using a modified Billard reagent ( p -ClPhNHSCF _(3) ) with oxidation of aryl trifluoromethyl sulfides using 1.2 equiv. of 30% aqueous hydrogen peroxide and this one-pot process has superior yields than would have been obtained in a two step process.

机译：过氧化氢用于氧化各种芳基三氟甲基硫化物。三氟乙酸用作活化溶剂，其能够实现非催化的氧化并增加亚砜形成的选择性。如通过氧化的TFA所示，增强了氧化剂的亲电特征，并抑制了亚砜基的进一步氧化。我们使用改性的钢结构试剂（p-clphnhscf _（3））加入了三氟甲基神经酰胺，其使用1.2当量氧化三氟甲基硫化物氧化。 30％过氧化氢水溶液和该1罐过程具有优于在两个步骤过程中获得的优异收率。

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《RSC Advances》 |2020年第57期|共7页
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Monika Horvat; Gregor Kodri?; Marjan Jereb; Jernej Iskra;
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1. One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide [J] . Horvat Monika, Kodric Gregor, Jereb Marjan, RSC Advances . 2020,第57期

机译：三氟甲基芳基三氟甲基芳基聚乙烯化合物与过氧化氢氧化的一个罐合成三氟甲基亚砜
2. Synthesis of 2-aryl-2-trifluoromethyl-1,3-thiazolidin-4-ones and 2-aryl-2-trifluoromethyltetrahydro-4H-1,3-thiazin-4-ones and their oxidation with hydrogen peroxide [J] . Melnichenko N. V., Bentya A. V., Rusanov E. B., Russian Journal of General Chemistry . 2015,第6期

机译：2-芳基-2-三氟甲基-1,3-噻唑烷-4-酮和2-芳基-2-三氟甲基四氢-4H-1,3-噻嗪-4-酮的合成及过氧化氢的氧化
3. Development of a preparative-scale asymmetric synthesis of (R)-p-tolyl methyl sulfoxide for use in a one-pot synthesis of a drug intermediate containing a trifluoromethyl-substituted alcohol functionality [J] . Han ZX, Song JHJ, Yee NK, Organic process research & development . 2007,第3期

机译：用于一锅合成包含三氟甲基取代的醇官能团的药物中间体的（R）-对甲苯基甲基亚砜的制备规模不对称合成的开发
4. Ultrafast kinetics subsequent to shock in an unreacted, oxygen balanced mixture of nitromethane and hydrogen peroxide [C] . Michael R. Armstrong, Joseph M. Zaug, Christian D. Grant International Detonation Symposium . 2018

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5. Methodological and comparative studies on directed ortho metallation of aryl tert-butyl sulfoxides and Ni(0)-catalyzed cross-coupling of aryl triflates and O-aryl carbamates. Studies directed toward the total synthesis of sterigmatocystin. [D] . Quesnelle, Claupe A. 1996

机译：方法学和比较研究的芳基叔丁基亚砜的定向原位金属化和芳基三氟甲磺酸酯和O-芳基氨基甲酸酯的Ni（0）催化的交叉偶联。研究针对全囊藻毒素的合成。
6. A Facile One-Pot Synthesis of Au/Cu2O Nanocomposites for Nonenzymatic Detection of Hydrogen Peroxide [O] . Ting Chen, Liangliang Tian, Yuan Chen, 2015

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7. One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide [O] . Monika Horvat, Gregor Kodrič, Marjan Jereb, 2020

机译：三氟甲基芳基三氟甲基芳基聚乙烯化合物与过氧化氢氧化的一个罐合成三氟甲基亚砜

One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide

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