钯催化异腈参与的交叉偶联反应研究
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摘要
发展简便直接的方法从廉价易得的原料合成复杂多官能团的有机分子是现代有机合成化学的研究热点之一。异腈是有机合成中一类非常有用的C1源，并广泛应用于形式多样的反应体系之中，尤其是在异腈参与的多组分反应（IMCR）中取得了显著成果。
众所周知，CO经常用于钯催化的串联反应中，并原子经济性的构建了一系列的羰基化合物和多种非常重要的杂环类化合物。异腈作为CO的等电子体，其结构和性质上也应该与CO类似，应该可以在钯催化体系下发生相似的化学反应。然而，在过去的几十年里，人们只关注了异腈的亲核性和亲电性在多组分反应中应用于含氮杂环类化合物的构建，而对于钯催化体系下中异腈的迁移插入反应研究甚少。基于此，我们意识到钯催化体系下异腈参与的交叉偶联反应理应在构建结构丰富多样的含氮化合物中显示其应有的价值。
本论文系统阐述了我们近几年在异腈化学中的研究成果。从构建新的碳-碳键和碳-氮键入手，我们发展了一系列的钯催化异腈参与的交叉偶联反应，并成功的构建了酰胺及多种含氮杂环类化合物。这些研究成果将分为五部分逐一介绍。
第二章研究了钯催化芳基卤与异腈通过碳-碳键的交叉偶联反应构建了一系列的芳基酰胺衍生物，该合成方法与传统的酰胺的合成路径完全不同。值得注意的是，该反应底物适用性十分广泛，对于烯基溴和苄基溴等底物同样适用，而且产物分离收率都比较好。这是一种全新的简易而高效的合成芳基酰胺类衍生物的方法。此方法的最大优点在于避免了使用有毒性且不易操作的CO气体或者酰氯及胺类原料的使用，在反应过程中异腈既提供了羰基源又提供了氨基源。
第三章研究了钯催化邻卤代苯甲酰氯或邻卤代苯磺酰氯、胺、异腈三组分通过两步一锅法的串联反应立体专一性的构建亚胺异吲哚酮及硫代亚胺异吲哚啉-1,1-二氧化物衍生物。其次，该反应体系还可以应用于6-氨基啡啶和11-氨基-二苯并氮氧杂卓类衍生物的构建，这类杂环化合物的合成方法在步骤经济性上远优于之前文献所报道的方法。
第四章研究了钯催化炔溴、异腈、邻氨基苯酚三组分串联环化反应构建4-氨基苯并[b][1,4]氮氧杂卓衍生物的方法。该方法最大的优点在于实现了一步构建氨基苯并[b][1,4]氮氧杂卓衍生物，明显优于文献所报道的多步合成路径，该方法可以为人们提供构建具有类似骨架的天然产物和药物分子。
第五章研究了在不同的钯催化体系下，利用氧气氧化环化邻氨基苯酚与异腈为2-氨基苯并恶唑和3-氨基苯并噁唑啉类衍生物。该方法不仅原料简单易得而且底物适用性十分广泛。其次，利用氧气作氧化剂十分绿色经济。
第六章研究了利用钯催化氧气氧化异腈与2-炔基苯胺环化构建4-卤代-2-氨基喹啉衍生物的方法。该反应底物适用性广泛，而且该方法还可以应用于两步一锅法高效的构建6H-吲哚[2,3-b]并喹啉衍生物。
The development of general and efficient methodologies for the synthesis of complexmolecular skeletons is the central focus of mordern organic chemistry. Isocyanides areimportant C1building blocks in organic synthesis and these molecules are known to take partin several of different types of reaction, especially finding particular usefulness in a widevariety of isocyanide-based multicomponent reactions.
As know, CO is always used in palladium-catalyzed cascade reactions to increasemolecular complexity of the products by incorporating carbonyl groups and various importantheterocycles can be synthesised atom economically in this manner. Since isocyanide isisoelectronic with CO, it show similar reactivity towards palladium and undergo the samefundamental transformations. Surprisingly, the most reported achievements mainly focus onexploring the potential utility of the nucleophilicity and electrophilicity of isocyanides inmulticomponent reactions for the synthesis of nitrogen-containing compounds. However,migratory insertion of isocyanides in palladium catalysis is much less explored. Consequently,we presumed that palladium-catalyzed reactions involving isocyanide insertion should offertremendous opportunities for the synthesis of fine nitrogen-containing compounds.
In this context, we describe herein our recent explorations in the field of isocyanideschemistry. An array of broadly useful coupling methodologies has been developed for theformation of C-C and C-N bonds etc. We further describe the application of these methods tothe syntheses of complex systems, including the amides and various nitrogen-containingheterocycles. Our research on palladium-catalyzed cross-coupling reactions involvingisocyanides has led to a series of new results which will be presented in the following fivechapters.
In chapter two, a new and efficient method for synthesis of amides viapalladium-catalyzed C-C coupling of aryl halides with isocyanides is reported, by which aseries of amides were formed from readily available starting materials under mild conditions.This transformation could extend its use for synthesis of natural products and significantpharmaceuticals.
In chapter three, we successfully realized a palladium-catalyzed one-pot cyclizationreaction to construct (3E)-(imino)isoindolin-1-ones and (3E)-(imino)thiaiso-indoline1,1-dioxides by introducing ortho-reactive functional groups on aryl halides. Under optimalconditions, the cyclization reaction afforded the corresponding products in good to excellentyields (up to93%) with high stereospecificity. Notably, this transformation successfully extends its application for synthesis of phenanthridins and dibenzooxazepins. This newsynthetic protocol not only builds up an application platform for palladium-catalyzed C-Ccoupling of aryl halides with isocyanides, but also opens atom economic and step economicsynthetic routes for nitrogen-containing heterocyclic compounds with wide functional groupcompatibility.
In chapter four, a robust route to4-amine-benzo[b][1,4]oxazepines relying upon apalladium-catalyzed tandem reaction of o-aminophenols, bromoalkynes and isocyanides hasbeen developed. This chemistry presumably proceeds through the migratory insertion ofisocyanides into the vinyl-palladium intermediate as a key step.
In chapter five, a Pd-catalyzed aerobic oxidation of o-aminophenols and isocyanides tothe synthesis of2-aminobenzoxazoles and3-aminobenzoxazines has been achieved under airatmosphere. The procedure constructs2-aminobenzoxazoles and3-aminobenzoxazines withmoderate to excellent yields and a broad substrate scope. Apart from experimentalsimplicity, this methodology has advantages of mild reaction conditions and easily accessiblestarting materials. Furthermore, the utility of this method is also successfully applied to thesynthesis of other types of useful nitrogen heterocycles.
In chapter six, a robust and regioselective palladium-catalyzed intermolecular aerobicoxidative cyclization of2-ethynylanilines with isocyanides to the synthesis of4-halo-2-aminoquinolines is reported herein. The procedure constructs various4-halo-2-aminoquinolines with moderate to excellent yields and a broad substrate scope.Furthermore, this process could be easily extended to synthesis of various6H-indolo[2,3-b]quinolines via an intramolecular Buchwald-Hartwig cross-coupling reaction in two-stepone-pot manner.
众所周知，CO经常用于钯催化的串联反应中，并原子经济性的构建了一系列的羰基化合物和多种非常重要的杂环类化合物。异腈作为CO的等电子体，其结构和性质上也应该与CO类似，应该可以在钯催化体系下发生相似的化学反应。然而，在过去的几十年里，人们只关注了异腈的亲核性和亲电性在多组分反应中应用于含氮杂环类化合物的构建，而对于钯催化体系下中异腈的迁移插入反应研究甚少。基于此，我们意识到钯催化体系下异腈参与的交叉偶联反应理应在构建结构丰富多样的含氮化合物中显示其应有的价值。
本论文系统阐述了我们近几年在异腈化学中的研究成果。从构建新的碳-碳键和碳-氮键入手，我们发展了一系列的钯催化异腈参与的交叉偶联反应，并成功的构建了酰胺及多种含氮杂环类化合物。这些研究成果将分为五部分逐一介绍。
第二章研究了钯催化芳基卤与异腈通过碳-碳键的交叉偶联反应构建了一系列的芳基酰胺衍生物，该合成方法与传统的酰胺的合成路径完全不同。值得注意的是，该反应底物适用性十分广泛，对于烯基溴和苄基溴等底物同样适用，而且产物分离收率都比较好。这是一种全新的简易而高效的合成芳基酰胺类衍生物的方法。此方法的最大优点在于避免了使用有毒性且不易操作的CO气体或者酰氯及胺类原料的使用，在反应过程中异腈既提供了羰基源又提供了氨基源。
第三章研究了钯催化邻卤代苯甲酰氯或邻卤代苯磺酰氯、胺、异腈三组分通过两步一锅法的串联反应立体专一性的构建亚胺异吲哚酮及硫代亚胺异吲哚啉-1,1-二氧化物衍生物。其次，该反应体系还可以应用于6-氨基啡啶和11-氨基-二苯并氮氧杂卓类衍生物的构建，这类杂环化合物的合成方法在步骤经济性上远优于之前文献所报道的方法。
第四章研究了钯催化炔溴、异腈、邻氨基苯酚三组分串联环化反应构建4-氨基苯并[b][1,4]氮氧杂卓衍生物的方法。该方法最大的优点在于实现了一步构建氨基苯并[b][1,4]氮氧杂卓衍生物，明显优于文献所报道的多步合成路径，该方法可以为人们提供构建具有类似骨架的天然产物和药物分子。
第五章研究了在不同的钯催化体系下，利用氧气氧化环化邻氨基苯酚与异腈为2-氨基苯并恶唑和3-氨基苯并噁唑啉类衍生物。该方法不仅原料简单易得而且底物适用性十分广泛。其次，利用氧气作氧化剂十分绿色经济。
第六章研究了利用钯催化氧气氧化异腈与2-炔基苯胺环化构建4-卤代-2-氨基喹啉衍生物的方法。该反应底物适用性广泛，而且该方法还可以应用于两步一锅法高效的构建6H-吲哚[2,3-b]并喹啉衍生物。
The development of general and efficient methodologies for the synthesis of complexmolecular skeletons is the central focus of mordern organic chemistry. Isocyanides areimportant C1building blocks in organic synthesis and these molecules are known to take partin several of different types of reaction, especially finding particular usefulness in a widevariety of isocyanide-based multicomponent reactions.
As know, CO is always used in palladium-catalyzed cascade reactions to increasemolecular complexity of the products by incorporating carbonyl groups and various importantheterocycles can be synthesised atom economically in this manner. Since isocyanide isisoelectronic with CO, it show similar reactivity towards palladium and undergo the samefundamental transformations. Surprisingly, the most reported achievements mainly focus onexploring the potential utility of the nucleophilicity and electrophilicity of isocyanides inmulticomponent reactions for the synthesis of nitrogen-containing compounds. However,migratory insertion of isocyanides in palladium catalysis is much less explored. Consequently,we presumed that palladium-catalyzed reactions involving isocyanide insertion should offertremendous opportunities for the synthesis of fine nitrogen-containing compounds.
In this context, we describe herein our recent explorations in the field of isocyanideschemistry. An array of broadly useful coupling methodologies has been developed for theformation of C-C and C-N bonds etc. We further describe the application of these methods tothe syntheses of complex systems, including the amides and various nitrogen-containingheterocycles. Our research on palladium-catalyzed cross-coupling reactions involvingisocyanides has led to a series of new results which will be presented in the following fivechapters.
In chapter two, a new and efficient method for synthesis of amides viapalladium-catalyzed C-C coupling of aryl halides with isocyanides is reported, by which aseries of amides were formed from readily available starting materials under mild conditions.This transformation could extend its use for synthesis of natural products and significantpharmaceuticals.
In chapter three, we successfully realized a palladium-catalyzed one-pot cyclizationreaction to construct (3E)-(imino)isoindolin-1-ones and (3E)-(imino)thiaiso-indoline1,1-dioxides by introducing ortho-reactive functional groups on aryl halides. Under optimalconditions, the cyclization reaction afforded the corresponding products in good to excellentyields (up to93%) with high stereospecificity. Notably, this transformation successfully extends its application for synthesis of phenanthridins and dibenzooxazepins. This newsynthetic protocol not only builds up an application platform for palladium-catalyzed C-Ccoupling of aryl halides with isocyanides, but also opens atom economic and step economicsynthetic routes for nitrogen-containing heterocyclic compounds with wide functional groupcompatibility.
In chapter four, a robust route to4-amine-benzo[b][1,4]oxazepines relying upon apalladium-catalyzed tandem reaction of o-aminophenols, bromoalkynes and isocyanides hasbeen developed. This chemistry presumably proceeds through the migratory insertion ofisocyanides into the vinyl-palladium intermediate as a key step.
In chapter five, a Pd-catalyzed aerobic oxidation of o-aminophenols and isocyanides tothe synthesis of2-aminobenzoxazoles and3-aminobenzoxazines has been achieved under airatmosphere. The procedure constructs2-aminobenzoxazoles and3-aminobenzoxazines withmoderate to excellent yields and a broad substrate scope. Apart from experimentalsimplicity, this methodology has advantages of mild reaction conditions and easily accessiblestarting materials. Furthermore, the utility of this method is also successfully applied to thesynthesis of other types of useful nitrogen heterocycles.
In chapter six, a robust and regioselective palladium-catalyzed intermolecular aerobicoxidative cyclization of2-ethynylanilines with isocyanides to the synthesis of4-halo-2-aminoquinolines is reported herein. The procedure constructs various4-halo-2-aminoquinolines with moderate to excellent yields and a broad substrate scope.Furthermore, this process could be easily extended to synthesis of various6H-indolo[2,3-b]quinolines via an intramolecular Buchwald-Hartwig cross-coupling reaction in two-stepone-pot manner.
引文
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