新型三价碘化物的设计、合成与反应研究
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摘要
近年来,有机高价碘化学的研究引起了人们的广泛关注并得到了快速的发展。有机高价碘化物作为有机合成的试剂或催化剂不仅广泛应用于各类氧化反应中,还广泛应用于碳-碳键、碳-杂键及杂-杂键的形成,碳-氢键的活化、裂解及重排等反应中,在药物及中间体的制备和天然产物的全合成中也得到了非常广泛的应用,已发展成为一类拓展全新的合成方法学的新试剂。
但是尽管有机高价碘化物具有反应活性高、无毒安全及环境友好等优点,但高价碘化物的使用在许多方面却不符合绿色化学的要求,因为其参与的反应大多为化学计量的反应,反应结束后会生成等摩尔的氧化副产物碘苯或其衍生物,沸点较高,且在有机溶剂中溶解度很大,现行的处理方法一般需要在反应结束后通过柱层析进行分离,不仅给产物的分离及碘苯的回收再利用造成了困难,同时消耗了大量的有机溶剂,环境不友好。此外,许多高价碘化物参与的反应是在传统有机溶剂(如二氯甲烷、二甲基甲酰胺、二甲亚砜等)中进行的,对环境有潜在的危害性。
基于上述内容,本课题总体研究思路如下：首先,设计、合成一些新型的三价碘化物,并探索其在有机合成中的应用领域。其次,立足于现有已知的三价碘试剂,进一步拓展其在有机反应中的新应用。最后,针对目前有机高价碘化物使用上的一些缺点,从绿色化学的角度出发,分别研究了基于三价碘化物的负载体系、催化氧化体系及水相反应体系。
论文首先设计、合成了一系列烷氧基修饰的新型非环状丙二酸甲酯型及环状二甲酮型碘叶立德,X-ray单晶衍射表征证明了通过在碘苯的邻位引入烷氧基进行结构修饰,产生分子内二级碘氧键I…O作用力,削弱了分子间的碘氧键I…O作用力,从而显著降低了原化合物易聚合的性质,稳定性及溶解性显著提高。研究了经烷氧基修饰的碘叶立德在环丙烷化反应、C-H插入反应、转叶立德反应及与碳二亚胺的环加成反应中的应用。结果表明,经过改性后的新型碘叶立德无论在操作使用的便捷性上,还是在反应性能上较原化合物均有着明显的提高。
其次,立足于现有的已知三价碘化物,研究了它们在合成含碳杂不饱和键的氰基化合物及碳二亚胺类化合物中的新应用。系统考察了不同的三价碘化物、反应温度、反应时间、催化剂用量、溶剂种类等因素对上述反应的影响,研究表明,某些有机三价碘化物,特别是羟基对甲苯磺酸基碘苯(HTIB)能够有效的促进上述反应,具有反应条件温和、后处理简单、产率理想等优点。
最后,针对目前有机高价碘化物使用上的一些缺点,从绿色化学的角度出发,先研究了负载型三价碘化物的制备及应用,分别设计、合成了聚苯乙烯负载的二乙酰氧基碘苯及纳米三氧化二铁负载的二乙酰氧基碘苯,考察了它们在醇类氧化反应中的应用及其自身的循环回收使用性能。研究表明,这些负载型试剂具有较高的稳定性和氧化活性,在反应结束后经过简单的过滤或磁性分离,即可达到循环回收使用的目的,经多次的循环使用,未发现明显的失活现象。
针对负载型三价碘试剂的合成路线较繁琐等缺点,论文接着对基于三价碘化物的催化氧化体系进行了较为深入、系统的研究,分别探索了以间氯过氧苯甲酸、过硫酸钾、过氧乙酸和双氧水为助氧化剂,以碘苯或无机小分子碘化物四丁基碘化铵为催化剂,构建了反应条件温和、后处理简单及对环境友好的有效的催化氧化体系,并成功将其应用于醇类化合物的选择性氧化及苯并咪唑类衍生物的绿色合成中。
针对目前高价碘化物参与的反应大多需要使用对环境有潜在危害性的一些传统有机溶剂的缺点,论文研究了基于三价碘化物的绿色水相反应体系。分别探索了以溴化钾或β-环糊精为反应的催化剂,基于亚碘酰苯及其衍生物的水相中的醇类化合物的选择性氧化反应。与其他无过渡金属催化氧化体系相比,反应效率高,选择性好,且对环境更加友好。
During the past decade, the organic chemistry of hypervalent iodine compounds has experienced an unprecedented development. Hypervalent iodine reagents are nowadays popular reagents not only for the oxidation, but also for the formation of carbon-carbon bonds, carbon-heteroatom bonds, heteroatom-heteroatom bonds. Activation of carbon-hydrogen bonds, rearrangements and fragmentations can also be induced by these reagents. Therefore, hypervalent iodine compounds offer high potential for the improvement of known reactions, not only from the environmental point of view, they are also potentially interesting reagents for the development of completely new synthetic transformations.
Despite their useful reactivity, enhanced stability, and environmentally benign nature, common hypervalent iodine reagents are not perfect with respect to the principles of Green Chemistry. The reactions of these stoichiometric reagents with organic substrates lead to Arl as the byproduct, which is difficult to recover and reuse because of its high volatility and solubility in organic solvents. In addition, typical reactions of common hypervalent iodine reagents are performed in non-recyclable organic solvent (dichloromethane, DMF, DMSO, etc.), which have potentially damaging environmental properties.
In this dissertation, focused on the problems existed in the hypervalent iodine chemistry, applications of hypervalent iodine (Ⅲ) compounds in organic synthesis processes and their recycling approaches were investigated.
Some novel, highly soluble, and reactive iodonium ylides bearing an ortho substituent on the phenyl ring are designed and prepared from substituted iodobenzene and malonate or dimedone. According to X-ray crystal graphy, these novel iodonium ylides show remarkable intramolecular I…O interaction, which decreased the intermolecular I…O interaction and the tendency to polymerize. Therefore, they are highly soluble in common solvent and show higher reactivity than the original phenyliodonium ylides in the Rh-catalyzed cyclopropanation, C-H insertion, transylidation and reaction with carbodiimides.
As model reactions for the formation of carbon-heteroatom bonds, synthesis of nitriles and carbodiimides was then studied using hypervalent iodine (Ⅲ) compounds as reagents. It was found that, among various kinds of hypervalent iodine (III) reagents, HTIB is especially effective for these kinds of transformations. In the presence of HTIB and nitrogen source, alcohols, aldehydes and amines all converted to nitriles under mild conditions in high yields. The desulfidation of thiourea to carbodiimides also proceeded smothly under mild conditions in the presence of HTIB with high yields.
Polymer-supported and magnetic nanoparticle-supported PhI(OAc)2were successfully prepared and their applications and recycle abilities in oxidation of alcohols were studied in detail. Results showed that these supported reagents have good stability and catalytic activities, and they could be easily recovered and reused without significant loss of activities.
Catalyst oxidative systems using m-chloroperbenzoic acid, potassium peroxodisulfate, peracetic acid and hydrogen peroxide as co-oxidant were investigated. The applications of these systems in the oxidation of alcohols and the synthesis of benzimidazoles were explored.
The development of aqueous-phase reactions using hypervalent iodine (Ⅲ) compounds was also investigated. Selective oxidation of alcohols can be achieved using iodosylbenzene or its derivative as oxidant in the presence of β-Cyclodextrin or potassium bromide. These systems offers several advantages, including mild reaction conditions, simple work-up procedure and more environmentally benign.
但是尽管有机高价碘化物具有反应活性高、无毒安全及环境友好等优点,但高价碘化物的使用在许多方面却不符合绿色化学的要求,因为其参与的反应大多为化学计量的反应,反应结束后会生成等摩尔的氧化副产物碘苯或其衍生物,沸点较高,且在有机溶剂中溶解度很大,现行的处理方法一般需要在反应结束后通过柱层析进行分离,不仅给产物的分离及碘苯的回收再利用造成了困难,同时消耗了大量的有机溶剂,环境不友好。此外,许多高价碘化物参与的反应是在传统有机溶剂(如二氯甲烷、二甲基甲酰胺、二甲亚砜等)中进行的,对环境有潜在的危害性。
基于上述内容,本课题总体研究思路如下：首先,设计、合成一些新型的三价碘化物,并探索其在有机合成中的应用领域。其次,立足于现有已知的三价碘试剂,进一步拓展其在有机反应中的新应用。最后,针对目前有机高价碘化物使用上的一些缺点,从绿色化学的角度出发,分别研究了基于三价碘化物的负载体系、催化氧化体系及水相反应体系。
论文首先设计、合成了一系列烷氧基修饰的新型非环状丙二酸甲酯型及环状二甲酮型碘叶立德,X-ray单晶衍射表征证明了通过在碘苯的邻位引入烷氧基进行结构修饰,产生分子内二级碘氧键I…O作用力,削弱了分子间的碘氧键I…O作用力,从而显著降低了原化合物易聚合的性质,稳定性及溶解性显著提高。研究了经烷氧基修饰的碘叶立德在环丙烷化反应、C-H插入反应、转叶立德反应及与碳二亚胺的环加成反应中的应用。结果表明,经过改性后的新型碘叶立德无论在操作使用的便捷性上,还是在反应性能上较原化合物均有着明显的提高。
其次,立足于现有的已知三价碘化物,研究了它们在合成含碳杂不饱和键的氰基化合物及碳二亚胺类化合物中的新应用。系统考察了不同的三价碘化物、反应温度、反应时间、催化剂用量、溶剂种类等因素对上述反应的影响,研究表明,某些有机三价碘化物,特别是羟基对甲苯磺酸基碘苯(HTIB)能够有效的促进上述反应,具有反应条件温和、后处理简单、产率理想等优点。
最后,针对目前有机高价碘化物使用上的一些缺点,从绿色化学的角度出发,先研究了负载型三价碘化物的制备及应用,分别设计、合成了聚苯乙烯负载的二乙酰氧基碘苯及纳米三氧化二铁负载的二乙酰氧基碘苯,考察了它们在醇类氧化反应中的应用及其自身的循环回收使用性能。研究表明,这些负载型试剂具有较高的稳定性和氧化活性,在反应结束后经过简单的过滤或磁性分离,即可达到循环回收使用的目的,经多次的循环使用,未发现明显的失活现象。
针对负载型三价碘试剂的合成路线较繁琐等缺点,论文接着对基于三价碘化物的催化氧化体系进行了较为深入、系统的研究,分别探索了以间氯过氧苯甲酸、过硫酸钾、过氧乙酸和双氧水为助氧化剂,以碘苯或无机小分子碘化物四丁基碘化铵为催化剂,构建了反应条件温和、后处理简单及对环境友好的有效的催化氧化体系,并成功将其应用于醇类化合物的选择性氧化及苯并咪唑类衍生物的绿色合成中。
针对目前高价碘化物参与的反应大多需要使用对环境有潜在危害性的一些传统有机溶剂的缺点,论文研究了基于三价碘化物的绿色水相反应体系。分别探索了以溴化钾或β-环糊精为反应的催化剂,基于亚碘酰苯及其衍生物的水相中的醇类化合物的选择性氧化反应。与其他无过渡金属催化氧化体系相比,反应效率高,选择性好,且对环境更加友好。
During the past decade, the organic chemistry of hypervalent iodine compounds has experienced an unprecedented development. Hypervalent iodine reagents are nowadays popular reagents not only for the oxidation, but also for the formation of carbon-carbon bonds, carbon-heteroatom bonds, heteroatom-heteroatom bonds. Activation of carbon-hydrogen bonds, rearrangements and fragmentations can also be induced by these reagents. Therefore, hypervalent iodine compounds offer high potential for the improvement of known reactions, not only from the environmental point of view, they are also potentially interesting reagents for the development of completely new synthetic transformations.
Despite their useful reactivity, enhanced stability, and environmentally benign nature, common hypervalent iodine reagents are not perfect with respect to the principles of Green Chemistry. The reactions of these stoichiometric reagents with organic substrates lead to Arl as the byproduct, which is difficult to recover and reuse because of its high volatility and solubility in organic solvents. In addition, typical reactions of common hypervalent iodine reagents are performed in non-recyclable organic solvent (dichloromethane, DMF, DMSO, etc.), which have potentially damaging environmental properties.
In this dissertation, focused on the problems existed in the hypervalent iodine chemistry, applications of hypervalent iodine (Ⅲ) compounds in organic synthesis processes and their recycling approaches were investigated.
Some novel, highly soluble, and reactive iodonium ylides bearing an ortho substituent on the phenyl ring are designed and prepared from substituted iodobenzene and malonate or dimedone. According to X-ray crystal graphy, these novel iodonium ylides show remarkable intramolecular I…O interaction, which decreased the intermolecular I…O interaction and the tendency to polymerize. Therefore, they are highly soluble in common solvent and show higher reactivity than the original phenyliodonium ylides in the Rh-catalyzed cyclopropanation, C-H insertion, transylidation and reaction with carbodiimides.
As model reactions for the formation of carbon-heteroatom bonds, synthesis of nitriles and carbodiimides was then studied using hypervalent iodine (Ⅲ) compounds as reagents. It was found that, among various kinds of hypervalent iodine (III) reagents, HTIB is especially effective for these kinds of transformations. In the presence of HTIB and nitrogen source, alcohols, aldehydes and amines all converted to nitriles under mild conditions in high yields. The desulfidation of thiourea to carbodiimides also proceeded smothly under mild conditions in the presence of HTIB with high yields.
Polymer-supported and magnetic nanoparticle-supported PhI(OAc)2were successfully prepared and their applications and recycle abilities in oxidation of alcohols were studied in detail. Results showed that these supported reagents have good stability and catalytic activities, and they could be easily recovered and reused without significant loss of activities.
Catalyst oxidative systems using m-chloroperbenzoic acid, potassium peroxodisulfate, peracetic acid and hydrogen peroxide as co-oxidant were investigated. The applications of these systems in the oxidation of alcohols and the synthesis of benzimidazoles were explored.
The development of aqueous-phase reactions using hypervalent iodine (Ⅲ) compounds was also investigated. Selective oxidation of alcohols can be achieved using iodosylbenzene or its derivative as oxidant in the presence of β-Cyclodextrin or potassium bromide. These systems offers several advantages, including mild reaction conditions, simple work-up procedure and more environmentally benign.
引文
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