Recyclable iron(ii) caffeine-derived ionic salt catalyst in the Diels–Alder reaction of cyclopentadiene and α,β-unsaturated N-acyl-oxazolidinones in dimethyl carbonate

Di Meng; Dazhi Li; Thierry Ollevier

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Recyclable iron(ii) caffeine-derived ionic salt catalyst in the Diels–Alder reaction of cyclopentadiene and α,β-unsaturated N-acyl-oxazolidinones in dimethyl carbonate

机译：可再循环的铁（II）咖啡因衍生的离子盐催化剂在碳酸二甲基酯中环戊二烯和α，β-不饱和N-酰基 - 恶唑烷酮的酰胺反应中的反应

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Iron( II ) triflate was used in combination with caffeine-derived salts as recyclable catalysts for the Diels–Alder reaction run in dimethyl carbonate (DMC) as a green solvent. The catalyst was prepared as an ionic salt from a xanthinium salt and Fe(OTf) _(2) . Various substrates including α,β-unsaturated carbonyl and N -acyloxazolidinone derivatives were reacted with cyclopentadiene using this recyclable catalyst. The use of a low catalyst loading (1 mol%) afforded high yields (up to 99%) of the corresponding cycloadducts. The recycling and the efficiency of the catalyst were demonstrated for several runs.

机译：铁（II）三氟甲酸酯与咖啡因衍生的盐组合使用，作为Diels- alder反应的可回收催化剂，以碳酸二甲酯（DMC）为绿色溶剂。将催化剂制备为来自黄嘌呤盐和Fe（OTF）_（2）的离子盐。使用该可回收催化剂与环戊二烯反应，包括α，β-不饱和羰基和N-酰胺唑烷基酮衍生物的各种底物与环戊二烯反应。使用低催化剂负载（1mol％），得到高产率（高达99％）的相应环形化合物。催化剂的再循环和效率进行了几次运行。

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《RSC Advances》 |2019年第38期|共8页
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Di Meng; Dazhi Li; Thierry Ollevier;
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1. Recyclable iron(ii) caffeine-derived ionic salt catalyst in the Diels-Alder reaction of cyclopentadiene and alpha,beta-unsaturated N-acyl-oxazolidinones in dimethyl carbonate [J] . Meng Di, Li Dazhi, Ollevier Thierry RSC Advances . 2019,第38期

机译：可再循环的铁（II）咖啡因衍生的离子盐催化剂在碳酸二甲基酯中环戊二烯和α-不饱和的N-酰基 - 恶唑烷酮的二氧化铝反应
2. Asymmetric diels-alder and inverse-electron-demand hetero-Diels-Alder reactions of β,γ-unsaturated α-ketoesters with cyclopentadiene catalyzed by N,N′-dioxide copper(II) complex [J] . Zhu Y., Chen X., Xie M., Chemistry: A European journal . 2010,第39期

机译：N，N'-二氧化铜（II）配合物催化β，γ-不饱和α-酮酸酯与环戊二烯的不对称狄尔斯-阿尔德反应和反电子需求杂狄尔斯-阿尔德反应
3. Asymmetric Diels–Alder and Inverse-Electron-Demand Hetero-Diels–Alder Reactions of β,-Unsaturated -Ketoesters with Cyclopentadiene Catalyzed by N,N′-Dioxide Copper(II) Complex [J] . Yin Zhu Xiaohong Chen Mingsheng Xie Shunxi Dong Zhen Qiao Dr. Lili Lin Dr. Xiaohua Liu Prof. Dr. Xiaoming Feng Chemistry - A European Journal . 2010,第39期

机译：N，N'-二氧化铜（II）配合物催化β，-不饱和酮酸酯与环戊二烯的不对称Diels-Alder和电子反需求杂Diels-Alder反应
4. Transition Structure Models of Organic Reactions in Chloroaluminate Ionic Liquids: Cyclopentadiene and Methyl Acrylate Diels-Alder Reaction in Acidic and Basic Melts of 1-Ethyl-3-methylimidazolium Chloride with Aluminum(Ⅲ) Chloride [C] . Orlando Acevedo, Jeffrey D. Evanseck, American Chemical Society, Symposium ionic liquids as green solvents: Progress and prospects . 2003

机译：氯铝酸铝离子液体有机反应的过渡结构模型：氯化铝（Ⅲ）氯化铝酸性和碱性熔体中的环戊二烯和丙烯酸甲基丙烯酸甲基丙烯酸甲酯反应
5. I. New Methodologies and Catalysts for the Diels—Alder Reaction II. Computational and Synthetic Studies Toward the Total Synthesis of (–)-Stenine III. Synthetic Studies Toward the Total Syntheses of N-Methyl Welwitindolinone C isothiocyanate and N-Methyl Welwitindolinone B isothiocyanate [D] . Cleary, Leah 2013

机译：I. Diels-Alder反应的新方法和催化剂II。对（-）-Stenine III完全合成的计算和综合研究。 N-甲基韦尔吲哚啉酮C异硫氰酸酯的总合成的合成研究
6. Roles of Lewis Acid Catalysts in Diels‐Alder Reactions between Cyclopentadiene and Methyl Acrylate [O] . Prof. Ken Sakata, Prof. Emeritus Dr. Hiroshi Fujimoto 2020

机译：Lewis酸催化剂在环戊二烯与丙烯酸甲酯之间的Diels-Alder反应中的作用
7. Silica-supported chlorometallate(III) ionic liquids as recyclable catalysts for Diels–Alder reaction under solventless conditions [O] . Matuszek, Karolina, Chrobok, Anna, Latos, Piotr, 2016

机译：二氧化硅负载的金属氯离子（III）离子液体可作为无溶剂条件下Diels–Alder反应的可回收催化剂
8. Diels-Alder Reactions of 1,1-dimethyl-2,3,4,5-tetraphenyl-1-silacyclopentadiene, 1,1-dimethyl-2,5-diphenyl-1-silacyclopentadiene and 1,1-dimethyl-3,4-diphenyl-1-silacyclopentadiene with Maleic Anhydride; Kinetic Measurements [R] . Henry, G. K., Shinimoto, R., Zhou, Q., 1988

机译：1,1-二甲基-2,3,4,5-四苯基-1-硅杂环戊二烯，1,1-二甲基-2,5-二苯基-1-硅杂环戊二烯和1,1-二甲基-3,4的二烯 - 炔反应 - 二苯基-1-硅杂环戊二烯与马来酸酐;动力学测量

Recyclable iron(ii) caffeine-derived ionic salt catalyst in the Diels–Alder reaction of cyclopentadiene and α,β-unsaturated N-acyl-oxazolidinones in dimethyl carbonate

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