钯催化芳基卤代烷与醇的分子内偶联反应
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摘要
过渡金属钯Pd催化C-C的交叉偶联反应,即芳基卤代烷与以C原子为中心的亲核试剂的反应,条件温和而且具有对多官能团的兼容性,这类偶联反应已经拓展到其它亲核试剂如胺类和硫醇类。然而,虽然含有氧的杂环芳基醚大量存在于具有药理活性的大分子中,但是钯Pd催化的芳基卤代烷与醇类偶联反应只是在一个难懂和摸索的阶段。现在合成芳基醚的通用方法是芳基卤代烷与醇直接进行亲核反应,但是这个反应的条件非常苛刻而且需要大量的醇并且只限制在底物水平。
本文首先介绍过渡金属钯Pd催化的C-C偶联的研究近况,主要是各类典型人名反应(Heck反应,Sonogashira反应,Stille反应、Suzuki反应和Negishi反应)的基本概念,反应的基本机理,发展概况和实际应用等方面的文献综述。在熟悉钯催化下C-C偶联反应的基础上,分过渡金属钯和其它过渡金属催化下碳-杂原子偶联(C-N,C-S,C-O等)中反应机理的阐述、同类反应的研究进展、各方面反应条件的选择和其在有机合成中的重要应用等方面的内容进行综述。
事实上,虽然醇盐的亲核性不如胺类或硫醇类化合物,更不如各种所谓的“强”金属有机亲核试剂,但是它们进行分子间和分子内偶联的基本机理是相通的。上面提到关于过渡金属钯Pd催化的C-C和C-杂原子偶联两个方面的文献概述,对于了解和掌握钯催化下的各种偶联反应有很大的帮助,对于找到更高效和更快速的分子间偶联和分子内偶联的方法,特别是本文所涉及到的钯Pd催化的卤代芳烃和醇的分子内偶联的合成工作具有关键的指导作用。
第三章中,首先介绍了C-N和C-O分子内偶联的相关研究成果,然后详细介绍了通过卤代芳烃与醇类的分子内偶联制备具有生物活性的1,3-氧氮杂卓的杂环类化合物。在这个研究过程中,不断摸索和优化分子内芳基醚的合成条件和步骤,最终得出了构建含有哒嗪酮骨架部分的氧氮杂卓环体系的最佳反应条件:以醋酸钯Pd(OAc)_2作为钯催化剂的来源,1,1'-bis(diphenylphosphino)-ferrocene(DPPF)作为金属钯的配体,碳酸钾K_2CO_3作为碱,在80℃的甲苯溶剂中进行反应。采用如上的实验条件,可以更加有效地合成出实际生产中用到的化合物中间体,而这些中间体及其衍生物都是具有药物活性的天然产物中非常重要或关键的部分,有着广泛的应用。
Palladium-catalyzed C-C bond formations,aryl halides reacting with carbon nucleophiles centered on carbon atom,have the advantage of mild reaction conditions and high functional group compatibility.Successful extension of these reactions to heteroatom nucleophiles including amines and thiols has been achieved.However,the research on palladium-catalyzed coupling of Ar-X with alcohols remains in a subtle and elusive period.Now,available methods for the synthesis of aryl ethers via direct nucleophilic substitution of an aryl halide with an alcohol typically require harsh or restrictive reaction conditions or a large excess of the alcohol and are limited in substrate scope.
First of all,this thesis summarizes the research about the transitional metal palladium-catalyzed C-C bond formations,emphasizing all kinds of typical coupling reactions named after famous chemists.The basic concepts,reaction mechanism, general research process and practical application of these coupling reactions, including Heck reaction,Sonogashira reaction,Stille reaction,Suzuki reaction and Negishi reaction,were elaborated one by one.Then,on the basis of mastery of palladium-catalyzed C-C coupling reaction,research process,reaction mechanism and condition of C-Heteroatom(C-N,C-S,C-O)coupling reactions catalyzed by Palladium and other transitional metals,including their great application in synthetic work,are summarized.
Although alkoxides are less nucleophilic than amines and thiols,let alone all kinds of 'hard' organometallic nucleophiles,the basic mechanism of inter- and intramolecule coupling reactions is similar.The aforementioned research process on palladium-catalyzed C-C and C-Heteroatom bond formations would be greatly helpful to understand and master all kinds of coupling reactions.Also,it is crucial for us to obtain more effective and efficient methods of inter- and intramolecule coupling, especially palladium-catalyzed intramolecule coupling of aryl halides with alcohols mentioned in this thesis.
In Chapter Three,research results of C-N and C-O bond formations by intromolecule coupling reaction have been summarized,then novel formation of 1,3-oxazepine heterocycles via palladium-catalyzed intramolecular coupling reaction is specified.In this process,we optimized reactions conditions and steps of synthesis of aryl ethers,and finally obtained the best conditions for this reaction:Pd(OAc)_2 as a palladium source,1,1'-bis(diphenylphosphino)-ferrocene(DPPF)as the ligand,and K_2CO_3 as base at 80℃in toluene.The products have potential applications as biological and medicinal relevant compounds.
本文首先介绍过渡金属钯Pd催化的C-C偶联的研究近况,主要是各类典型人名反应(Heck反应,Sonogashira反应,Stille反应、Suzuki反应和Negishi反应)的基本概念,反应的基本机理,发展概况和实际应用等方面的文献综述。在熟悉钯催化下C-C偶联反应的基础上,分过渡金属钯和其它过渡金属催化下碳-杂原子偶联(C-N,C-S,C-O等)中反应机理的阐述、同类反应的研究进展、各方面反应条件的选择和其在有机合成中的重要应用等方面的内容进行综述。
事实上,虽然醇盐的亲核性不如胺类或硫醇类化合物,更不如各种所谓的“强”金属有机亲核试剂,但是它们进行分子间和分子内偶联的基本机理是相通的。上面提到关于过渡金属钯Pd催化的C-C和C-杂原子偶联两个方面的文献概述,对于了解和掌握钯催化下的各种偶联反应有很大的帮助,对于找到更高效和更快速的分子间偶联和分子内偶联的方法,特别是本文所涉及到的钯Pd催化的卤代芳烃和醇的分子内偶联的合成工作具有关键的指导作用。
第三章中,首先介绍了C-N和C-O分子内偶联的相关研究成果,然后详细介绍了通过卤代芳烃与醇类的分子内偶联制备具有生物活性的1,3-氧氮杂卓的杂环类化合物。在这个研究过程中,不断摸索和优化分子内芳基醚的合成条件和步骤,最终得出了构建含有哒嗪酮骨架部分的氧氮杂卓环体系的最佳反应条件:以醋酸钯Pd(OAc)_2作为钯催化剂的来源,1,1'-bis(diphenylphosphino)-ferrocene(DPPF)作为金属钯的配体,碳酸钾K_2CO_3作为碱,在80℃的甲苯溶剂中进行反应。采用如上的实验条件,可以更加有效地合成出实际生产中用到的化合物中间体,而这些中间体及其衍生物都是具有药物活性的天然产物中非常重要或关键的部分,有着广泛的应用。
Palladium-catalyzed C-C bond formations,aryl halides reacting with carbon nucleophiles centered on carbon atom,have the advantage of mild reaction conditions and high functional group compatibility.Successful extension of these reactions to heteroatom nucleophiles including amines and thiols has been achieved.However,the research on palladium-catalyzed coupling of Ar-X with alcohols remains in a subtle and elusive period.Now,available methods for the synthesis of aryl ethers via direct nucleophilic substitution of an aryl halide with an alcohol typically require harsh or restrictive reaction conditions or a large excess of the alcohol and are limited in substrate scope.
First of all,this thesis summarizes the research about the transitional metal palladium-catalyzed C-C bond formations,emphasizing all kinds of typical coupling reactions named after famous chemists.The basic concepts,reaction mechanism, general research process and practical application of these coupling reactions, including Heck reaction,Sonogashira reaction,Stille reaction,Suzuki reaction and Negishi reaction,were elaborated one by one.Then,on the basis of mastery of palladium-catalyzed C-C coupling reaction,research process,reaction mechanism and condition of C-Heteroatom(C-N,C-S,C-O)coupling reactions catalyzed by Palladium and other transitional metals,including their great application in synthetic work,are summarized.
Although alkoxides are less nucleophilic than amines and thiols,let alone all kinds of 'hard' organometallic nucleophiles,the basic mechanism of inter- and intramolecule coupling reactions is similar.The aforementioned research process on palladium-catalyzed C-C and C-Heteroatom bond formations would be greatly helpful to understand and master all kinds of coupling reactions.Also,it is crucial for us to obtain more effective and efficient methods of inter- and intramolecule coupling, especially palladium-catalyzed intramolecule coupling of aryl halides with alcohols mentioned in this thesis.
In Chapter Three,research results of C-N and C-O bond formations by intromolecule coupling reaction have been summarized,then novel formation of 1,3-oxazepine heterocycles via palladium-catalyzed intramolecular coupling reaction is specified.In this process,we optimized reactions conditions and steps of synthesis of aryl ethers,and finally obtained the best conditions for this reaction:Pd(OAc)_2 as a palladium source,1,1'-bis(diphenylphosphino)-ferrocene(DPPF)as the ligand,and K_2CO_3 as base at 80℃in toluene.The products have potential applications as biological and medicinal relevant compounds.
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