银促进的自由基氟代及三氟甲硫基化反应研究
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摘要
含氟有机化合物是一类非常重要的化合物,在医药、农药等方面都有很重要的作用。我们采用银催化氧化的方法,实现了脂肪酸的脱羧氟代反应；采用银氧化激发三氟甲硫基自由基,活化烯烃捕捉完成了羟吲哚的制备；结合钯催化碳-氢活化和三氟甲硫基自由基氧化,实现了碳-氢三氟甲硫基化反应。
本论文共分四章。
第1章：碳-氟和碳-三氟甲硫基形成反应的研究进展
对于氟原子的引入反应,我们介绍了近年来的关于芳基氟以及烷基氟的合成进展,特别是金属催化或者参与的一系列反应,还综述了近年来自由基氟代的方法；而对于三氟甲硫基化反应,我们综述了近年来发展的直接亲核或者亲电三氟甲硫基化方法。
第2章：银催化脂肪酸脱羧氟代反应。
位置选择性地构建碳(sp3)-氟键仍然面临着困难。我们在selectfluor氧化的条件下,实现了银催化的脂肪酸水相脱羧氟代反应,在温和条件下以满意的收率合成了烷基氟产物。这种自由基氟化方法不仅有效、方便,而且有非常好的化学选择性以及良官能团兼容性。对于机理进行研究,我们提出了一种新颖的三价银促进的单电子转移过程。
第3章：银促进的活化烯烃的芳基三氟甲硫基化反应。
对于三氟甲硫基基团的引入,传统上主要通过一些间接的方法,而直接三氟甲硫基化则主要采用亲核或亲电的途径,有关三氟甲硫基自由基的研究却很少见。我们发展了一个新颖的银促进的三氟甲硫基化自由基激发方式,实现了三氟甲硫基羟吲哚化合物的方便合成。机理研究证实了该转化是通过三氟甲硫基自由基加成启动的串联反应。
第4章：吡啶导向碳-氢活化三氟甲硫基化反应。
在发展了银氧化激发三氟甲硫基自由基方法的基础上,我们结合钯催化碳-氢活化,通过三氟甲基自由基氧化碳-氢活化形成的二价环钯物种,形成高价钯后还原消除,实现了碳-氢直接三氟甲硫基化反应。区别于铜促进碳-氢活化方法给出的双取代三氟甲硫基化产物,这种方法可以选择性地得到单取代产物。
Fluorine-containing compounds have been widely used in pharmaceuticals, agrochemicals and materials because of their unique lipophilicity and bioactivities. We reported here a silver-catalyzed decarboxylative fluorination of various aliphatic carboxylic acids with selectfluor reagent in aqueous solution, a silver-mediated oxidative aryltrifluoromethylthiolation of activated alkenes to produce valuable trifluoromethylthiolated oxindoles, and a Pd-catalyzed C-H trifluromethylthiolation via a trifluoromethylthiol radical oxidation of palladiumcycle generated from C-H activation.
This dissertation includes four chapters.
Chapter1:Research progress of C-F and C-SCF3bonds formations For the introduction of fluorine atom, we reviewd recent C(sp2)-F and C(sp3)-F bonds foramtions, especially for Pd, Ag-catalyzed or-mediated reactions, and the radical fluorination methods. For the introduction of SCF3, we reviewed the progress of direct nucleophilic and electrophilic trifluoromethylthiolation developed in recent years.
Chapter2:Silver-catalyzed decarboxylative fluorination of aliphatic carboxylic acids in aqueous solution
Site-specific C(sp3)-F bond formations are still a challenging task. We developed here a Ag-catalyzed decarboxylative fluorination of aliphatic carboxylic acids with selectfluor reagent in aqueous solution, affording various alkyl fluorides in satisfactory yields under mild conditions. This efficient radical fluorination method shows good chemoselectivity and functional-group tolerance. A mechanism involvinig Ag(Ⅲ)-mediated single electron transfer followed by fluorine atom transfer is proposed for this catalytic fluorodecarboxylation.
Chapter3:Silver-mediated radical aryltrifluoromethylthiolaton of activated alkenes
Although a diverse array of organic molecules were trifluoromethylthiolated by the nucleophilic and electrophilic CF3S reagents, the F3CS· radical-type pathway remains less explored. We developed the first example of silver-mediated oxidative aryltrifluoromethylthiolation of activated alkenes to produce valuable trifluoromethylthiole-containing oxindoles. Mechanistic investigations indicated that this novel transformation proceeded through a unique F3CS· radical addition path, thus providing a practical and easy-handling method to generate a F3CS· radical in the laboratory.
Chapter4:Ag-mediated Pd-catalyzed radical C-H trifluoromethylthiolation of2-phenylpyridine
With the new silver-mediated trifluoromethylthio radical-generating method, we developed a palladium-catalyzed C-H trifluoromethylthiolation via C-SCF3reductive elimination from high valent Pd species, which formed through the trifluoromethylthio radical oxidation of cyclopalladium after the C-H activation. Different from the previous report on copper-mediated C-H trifluoromethylthiolation, this newly developd method could furnish mono-substituted products.
本论文共分四章。
第1章：碳-氟和碳-三氟甲硫基形成反应的研究进展
对于氟原子的引入反应,我们介绍了近年来的关于芳基氟以及烷基氟的合成进展,特别是金属催化或者参与的一系列反应,还综述了近年来自由基氟代的方法；而对于三氟甲硫基化反应,我们综述了近年来发展的直接亲核或者亲电三氟甲硫基化方法。
第2章：银催化脂肪酸脱羧氟代反应。
位置选择性地构建碳(sp3)-氟键仍然面临着困难。我们在selectfluor氧化的条件下,实现了银催化的脂肪酸水相脱羧氟代反应,在温和条件下以满意的收率合成了烷基氟产物。这种自由基氟化方法不仅有效、方便,而且有非常好的化学选择性以及良官能团兼容性。对于机理进行研究,我们提出了一种新颖的三价银促进的单电子转移过程。
第3章：银促进的活化烯烃的芳基三氟甲硫基化反应。
对于三氟甲硫基基团的引入,传统上主要通过一些间接的方法,而直接三氟甲硫基化则主要采用亲核或亲电的途径,有关三氟甲硫基自由基的研究却很少见。我们发展了一个新颖的银促进的三氟甲硫基化自由基激发方式,实现了三氟甲硫基羟吲哚化合物的方便合成。机理研究证实了该转化是通过三氟甲硫基自由基加成启动的串联反应。
第4章：吡啶导向碳-氢活化三氟甲硫基化反应。
在发展了银氧化激发三氟甲硫基自由基方法的基础上,我们结合钯催化碳-氢活化,通过三氟甲基自由基氧化碳-氢活化形成的二价环钯物种,形成高价钯后还原消除,实现了碳-氢直接三氟甲硫基化反应。区别于铜促进碳-氢活化方法给出的双取代三氟甲硫基化产物,这种方法可以选择性地得到单取代产物。
Fluorine-containing compounds have been widely used in pharmaceuticals, agrochemicals and materials because of their unique lipophilicity and bioactivities. We reported here a silver-catalyzed decarboxylative fluorination of various aliphatic carboxylic acids with selectfluor reagent in aqueous solution, a silver-mediated oxidative aryltrifluoromethylthiolation of activated alkenes to produce valuable trifluoromethylthiolated oxindoles, and a Pd-catalyzed C-H trifluromethylthiolation via a trifluoromethylthiol radical oxidation of palladiumcycle generated from C-H activation.
This dissertation includes four chapters.
Chapter1:Research progress of C-F and C-SCF3bonds formations For the introduction of fluorine atom, we reviewd recent C(sp2)-F and C(sp3)-F bonds foramtions, especially for Pd, Ag-catalyzed or-mediated reactions, and the radical fluorination methods. For the introduction of SCF3, we reviewed the progress of direct nucleophilic and electrophilic trifluoromethylthiolation developed in recent years.
Chapter2:Silver-catalyzed decarboxylative fluorination of aliphatic carboxylic acids in aqueous solution
Site-specific C(sp3)-F bond formations are still a challenging task. We developed here a Ag-catalyzed decarboxylative fluorination of aliphatic carboxylic acids with selectfluor reagent in aqueous solution, affording various alkyl fluorides in satisfactory yields under mild conditions. This efficient radical fluorination method shows good chemoselectivity and functional-group tolerance. A mechanism involvinig Ag(Ⅲ)-mediated single electron transfer followed by fluorine atom transfer is proposed for this catalytic fluorodecarboxylation.
Chapter3:Silver-mediated radical aryltrifluoromethylthiolaton of activated alkenes
Although a diverse array of organic molecules were trifluoromethylthiolated by the nucleophilic and electrophilic CF3S reagents, the F3CS· radical-type pathway remains less explored. We developed the first example of silver-mediated oxidative aryltrifluoromethylthiolation of activated alkenes to produce valuable trifluoromethylthiole-containing oxindoles. Mechanistic investigations indicated that this novel transformation proceeded through a unique F3CS· radical addition path, thus providing a practical and easy-handling method to generate a F3CS· radical in the laboratory.
Chapter4:Ag-mediated Pd-catalyzed radical C-H trifluoromethylthiolation of2-phenylpyridine
With the new silver-mediated trifluoromethylthio radical-generating method, we developed a palladium-catalyzed C-H trifluoromethylthiolation via C-SCF3reductive elimination from high valent Pd species, which formed through the trifluoromethylthio radical oxidation of cyclopalladium after the C-H activation. Different from the previous report on copper-mediated C-H trifluoromethylthiolation, this newly developd method could furnish mono-substituted products.
引文
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