铟、镓试剂促进几类含羟基化合物的合成研究
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摘要
本论文主体部分共分两章。第一章对铟、镓试剂促进的有机反应作简要的综述,铟试剂主要介绍的几个重要部分：Barbier-type反应；Reformatsky-type反应；铟、钯试剂共同参与的反应；铟试剂的还原反应；三价铟促进的反应；活性铟促进的反应等。而镓试剂主要介绍其在Barbier-type反应中的应用；Reformatsky-type反应中的应用以及三氯化镓作为路易斯酸促进的几类反应。
第二章主要报道几类含羟基化合物的合成,共四部分。
首先本文研究了Sm/InCl3-4H2O体系现制的活性铟还原二苯基二硒醚得到硒负离子,进攻各类环氧化合物使之高选择性的开环,进而得到较高产率的相应β-羟基硒醚。我们的方法可以一锅法实现两步反应,同时可以在水相中进行,且反应的时间短。
其次本文以三氯化镓为催化剂,硫氰酸铵作为亲核试剂进攻各类环氧化合物,以极高的区域选择性得到90%左右产率的相应的开环产物p-羟基硫氰酯。我们的方法是以水作为介质,环境友好,且反应条件温和,提供了一条有价值的p-羟基硫氰酯的合成路线。
另外本文还研究了三氯化镓在纯水中促进的环氧化合物开环反应,以叠氮化钠作为亲核试剂,高产率、高选择性地得到相应的p-叠氮醇。
最后本文研究了铟单质促进无溶剂的Reformatsky-type反应,获得高产率的相应p-羟基酯和p-氨基酯。与以往的方法相比,环境友好(避免了溶剂的使用),条件温和,产率高,且能完全选择性的形成p-氨基酯而无相应的p-内酰胺。
The dissertation consists of two chapters.In the first chapter, indium reagents and gallium reagents promoted organic reactions are briefly described. First, some important organic reactions promoted by indium reagents are discussed, such as Barbier-type reactions, Reformatsky-type reactions, In-Pd promoting organic reactions, reduction, indium (Ⅲ) promoting reactions, active indium promoting reactions.Second, some important organic reactions promoted by gallium reagents are described: Barbier-type reactions,Reformatsky-type reactions, gallium (Ⅲ)-catalyzed organic reactions.
In the second chapter including four parts,a variety of compounds containing hydroxy group were prepared.Firstly, active indium generated in situ from Sm/InCl3-4H2O system reduce cleavage Se-Se bond and readily prepared phenyl selenide anion, then reacted easily with a variety of epoxides to afford the desiredβ-hydroxy selenides was reported.The notable advantages of the reactions are aqueous media, simple operation (one-pot) and neutral reaction conditions.
Sceondly, a facile and efficient protocol for the preparation ofβ-hydroxy thiocyanates through highly regioselective ring-opening epoxides with ammonium thiocyanate using gallium trichloride as a catalyst was described. The present method has some significant advantages,such as high yields (90%), environmentally benign process using water as media, mild reaction conditions, which quite competitive over other methods reported previously.
Thirdly, we continued to report gallium trichloride catalyzed highly regioselective ring-opening epoxides with NaN3 in water:a facile and green synthesis ofβ-azidoalchols in excellent yields.
Lastly, a convenient and efficient procedure for the solvent-free synthesis of P-hydroxy esters andβ-amino esters has been achieved by non-activated indium-mediated Reformatsky-type reaction of various aldehydes and aldimines at room temperature.Some significant advantages of the present method are environmentally benign process avoiding the use of solvents, excellent yields, mild reaction conditions, exclusive selectivity on forming theβ-amino esters and its abroad appilicability to various aldmines.
第二章主要报道几类含羟基化合物的合成,共四部分。
首先本文研究了Sm/InCl3-4H2O体系现制的活性铟还原二苯基二硒醚得到硒负离子,进攻各类环氧化合物使之高选择性的开环,进而得到较高产率的相应β-羟基硒醚。我们的方法可以一锅法实现两步反应,同时可以在水相中进行,且反应的时间短。
其次本文以三氯化镓为催化剂,硫氰酸铵作为亲核试剂进攻各类环氧化合物,以极高的区域选择性得到90%左右产率的相应的开环产物p-羟基硫氰酯。我们的方法是以水作为介质,环境友好,且反应条件温和,提供了一条有价值的p-羟基硫氰酯的合成路线。
另外本文还研究了三氯化镓在纯水中促进的环氧化合物开环反应,以叠氮化钠作为亲核试剂,高产率、高选择性地得到相应的p-叠氮醇。
最后本文研究了铟单质促进无溶剂的Reformatsky-type反应,获得高产率的相应p-羟基酯和p-氨基酯。与以往的方法相比,环境友好(避免了溶剂的使用),条件温和,产率高,且能完全选择性的形成p-氨基酯而无相应的p-内酰胺。
The dissertation consists of two chapters.In the first chapter, indium reagents and gallium reagents promoted organic reactions are briefly described. First, some important organic reactions promoted by indium reagents are discussed, such as Barbier-type reactions, Reformatsky-type reactions, In-Pd promoting organic reactions, reduction, indium (Ⅲ) promoting reactions, active indium promoting reactions.Second, some important organic reactions promoted by gallium reagents are described: Barbier-type reactions,Reformatsky-type reactions, gallium (Ⅲ)-catalyzed organic reactions.
In the second chapter including four parts,a variety of compounds containing hydroxy group were prepared.Firstly, active indium generated in situ from Sm/InCl3-4H2O system reduce cleavage Se-Se bond and readily prepared phenyl selenide anion, then reacted easily with a variety of epoxides to afford the desiredβ-hydroxy selenides was reported.The notable advantages of the reactions are aqueous media, simple operation (one-pot) and neutral reaction conditions.
Sceondly, a facile and efficient protocol for the preparation ofβ-hydroxy thiocyanates through highly regioselective ring-opening epoxides with ammonium thiocyanate using gallium trichloride as a catalyst was described. The present method has some significant advantages,such as high yields (90%), environmentally benign process using water as media, mild reaction conditions, which quite competitive over other methods reported previously.
Thirdly, we continued to report gallium trichloride catalyzed highly regioselective ring-opening epoxides with NaN3 in water:a facile and green synthesis ofβ-azidoalchols in excellent yields.
Lastly, a convenient and efficient procedure for the solvent-free synthesis of P-hydroxy esters andβ-amino esters has been achieved by non-activated indium-mediated Reformatsky-type reaction of various aldehydes and aldimines at room temperature.Some significant advantages of the present method are environmentally benign process avoiding the use of solvents, excellent yields, mild reaction conditions, exclusive selectivity on forming theβ-amino esters and its abroad appilicability to various aldmines.
引文
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