基于二硫缩烯酮α-位的碳—碳及碳—氧键偶联反应研究
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摘要
α-羰基二硫缩烯酮是一类多官能团有机中间体，广泛地用于构筑结构多样的碳环和杂环。经过一百多年的发展，α-羰基二硫缩烯酮化学已经成为有机化学领域重要研究课题之一。
二硫缩烯酮结构的多样性，决定了其化学性质的丰富性。其分子中由于β-位双烷硫基的推电子作用和α-羰基的拉电子作用，碳碳双键被高度极化，α-碳的电子云密度大大增加，因而具有很高的亲核性，可以和一系列的亲电试剂发生发应。α-官能团化反应是二硫缩烯酮的重要性质之一，近年来我们先后实现了基于二硫缩烯酮α-位的脱羧卤代和脱乙酰基卤代反应、Baylis-Hillman型反应、Michael加成反应、酰化反应、与醇的偶联反应以及多组分反应等等，并成功地将这些新反应应用到环己酮、不对称联苯、苯并呋喃、香豆素、吡啶衍生物、中氮茚、N-氧化吲哚等碳环和杂环的合成中。
碳碳偶联和碳杂原子偶联是有机合成化学研究领域中重要的研究内容。探索基于二硫缩烯酮α-位的新型碳碳偶联和碳杂原子偶联反应一直是我们课题组的主要研究目标。本论文对此进行了探索，论文内容主要包括如下：
1.实现了CuBr2催化的α-EWG二硫缩烯酮与苄醇类化合物的偶联反应（EWG: electron-withdrawing group），发展了一种从简单易得的原料出发，简便、高效地制备官能化4H-色烯和二氢香豆素的新方法。实验中发现，二硫缩烯酮分子中EWG的电子效应、反应所用溶剂等对反应有着重要的影响。通过溶剂的选择和反应时间的控制，可以选择性地合成4H-色烯和二氢香豆素。
2.实现了Pd(OAc)2催化下，以PhI(OAc)2为氧化剂，α-EWG二硫缩烯酮与简单羧酸的直接偶联反应，发展了一种合成羧酸烯酯的新方法。同时探索了偶联产物α-烯酰基-α-乙酰氧基二硫缩烯酮的Nazarov环合反应，证明了二硫缩烯酮α-位乙酰氧基的引入对Nazarov反应的活性和产物都有重要影响。
3.发展了经由α-EWG二硫缩烯酮、醛和对甲苯亚磺酸的三组分反应，高效合成烯丙基砜类物质的新方法。这是首次实现的活化烯烃的磺酰甲基化反应。所得产物是多官能团烯丙基砜类有机中间体，具有潜在的合成用途。
α-Oxo ketene-(S,S)acetals are versatile intermediates in organic synthesis andhave been widely applied in the construction of a diverse array of polysubstitutedcarbo-and heterocyclic compounds. After a hundred years of development, thechemistry of α-oxo ketene-(S,S)acetals has become an important research topic inorganic chemistry.
α-Oxo ketene-(S,S)acetals are valuable substrates with a variety of chemicalproperties owing to their structural diversity. The highly polarized push (dialkylthiogroup)-pull (electron-withdrawing group) interaction on the C C double bond ofα-oxo ketene-(S,S)acetals makes their α-carbon atom a potential nucleophilic center,and the coupling reaction at the nucleophilic α-carbon atom of these β,β-dialkylthioactivated alkenes is reliable and incorporates a wide variety of carbon and heteroatomelectrophiles. As an important property of α-oxo ketene-(S,S)acetals, in recent yearswe have realized halodecarboxylation, halodeacetylation, Baylis-Hillman reaction,Michael addition, acetylation, coupling reaction with alcohols, multi-componentreaction, etc. and has made great advances in the construction of a diverse array ofpolysubstituted carbo-and heterocyclic compounds, such as cyclohexanones,unsymmetrical biaryls, benzofurans, coumarins, pyridines, indolizines, indoleN-oxides, etc.
The C C bond forming reaction and carbon heteroatom bond coupling areimportant research contents in organic chemistry. The exploration of newcarbon carbon and carbon heteroatom bond forming reaction on α-C of α-oxoketene-(S,S)acetals has been the chief goal of our research. This thesis will show somenew exploratory work in this field and mainly includes three aspects:
1. Copper(II) bromide catalyzed C C coupling reaction of benzylic alcohols withα-Oxo ketene-(S,S)acetals have been realized, and we have developed a convenientsynthesis of polyfunctionalized4H-chromenes and dihydrocoumarins from the easilyavailable ketene dithioacetals and2-(hydroxymethyl)phenols. The protocol iscontrolled through the choice of solvents or the reaction time and features mildreaction conditions, high yields and multifunctionality of products.
2. Pd(OAc)2catalyzed direct coupling reactions of α-oxo ketene-(S,S)acetalswith carboxylic acids in the presence of PhI(OAc)2as an oxidant has been realized,and a new synthetic method for alkenyl esters was developed. α-Alkenoyl-α-acetoxy ketene-(S,S)-acetals, products of these C O coupling reactions, are good Nazarovcyclization substances, experimental results demonstrate that the α-alkenoyl groupsignificantly affects both the reactivity and products of the Nazarov cyclization.
3. An efficient synthesis of allylic sulfones via a threee-component reactioninvolving an α-oxo ketene-(S,S)acetal, an aldehyde and4-methylbenzenesulfinicacid was developed. It is the first example of sulfonylmethylation of activatedalkenes.
二硫缩烯酮结构的多样性，决定了其化学性质的丰富性。其分子中由于β-位双烷硫基的推电子作用和α-羰基的拉电子作用，碳碳双键被高度极化，α-碳的电子云密度大大增加，因而具有很高的亲核性，可以和一系列的亲电试剂发生发应。α-官能团化反应是二硫缩烯酮的重要性质之一，近年来我们先后实现了基于二硫缩烯酮α-位的脱羧卤代和脱乙酰基卤代反应、Baylis-Hillman型反应、Michael加成反应、酰化反应、与醇的偶联反应以及多组分反应等等，并成功地将这些新反应应用到环己酮、不对称联苯、苯并呋喃、香豆素、吡啶衍生物、中氮茚、N-氧化吲哚等碳环和杂环的合成中。
碳碳偶联和碳杂原子偶联是有机合成化学研究领域中重要的研究内容。探索基于二硫缩烯酮α-位的新型碳碳偶联和碳杂原子偶联反应一直是我们课题组的主要研究目标。本论文对此进行了探索，论文内容主要包括如下：
1.实现了CuBr2催化的α-EWG二硫缩烯酮与苄醇类化合物的偶联反应（EWG: electron-withdrawing group），发展了一种从简单易得的原料出发，简便、高效地制备官能化4H-色烯和二氢香豆素的新方法。实验中发现，二硫缩烯酮分子中EWG的电子效应、反应所用溶剂等对反应有着重要的影响。通过溶剂的选择和反应时间的控制，可以选择性地合成4H-色烯和二氢香豆素。
2.实现了Pd(OAc)2催化下，以PhI(OAc)2为氧化剂，α-EWG二硫缩烯酮与简单羧酸的直接偶联反应，发展了一种合成羧酸烯酯的新方法。同时探索了偶联产物α-烯酰基-α-乙酰氧基二硫缩烯酮的Nazarov环合反应，证明了二硫缩烯酮α-位乙酰氧基的引入对Nazarov反应的活性和产物都有重要影响。
3.发展了经由α-EWG二硫缩烯酮、醛和对甲苯亚磺酸的三组分反应，高效合成烯丙基砜类物质的新方法。这是首次实现的活化烯烃的磺酰甲基化反应。所得产物是多官能团烯丙基砜类有机中间体，具有潜在的合成用途。
α-Oxo ketene-(S,S)acetals are versatile intermediates in organic synthesis andhave been widely applied in the construction of a diverse array of polysubstitutedcarbo-and heterocyclic compounds. After a hundred years of development, thechemistry of α-oxo ketene-(S,S)acetals has become an important research topic inorganic chemistry.
α-Oxo ketene-(S,S)acetals are valuable substrates with a variety of chemicalproperties owing to their structural diversity. The highly polarized push (dialkylthiogroup)-pull (electron-withdrawing group) interaction on the C C double bond ofα-oxo ketene-(S,S)acetals makes their α-carbon atom a potential nucleophilic center,and the coupling reaction at the nucleophilic α-carbon atom of these β,β-dialkylthioactivated alkenes is reliable and incorporates a wide variety of carbon and heteroatomelectrophiles. As an important property of α-oxo ketene-(S,S)acetals, in recent yearswe have realized halodecarboxylation, halodeacetylation, Baylis-Hillman reaction,Michael addition, acetylation, coupling reaction with alcohols, multi-componentreaction, etc. and has made great advances in the construction of a diverse array ofpolysubstituted carbo-and heterocyclic compounds, such as cyclohexanones,unsymmetrical biaryls, benzofurans, coumarins, pyridines, indolizines, indoleN-oxides, etc.
The C C bond forming reaction and carbon heteroatom bond coupling areimportant research contents in organic chemistry. The exploration of newcarbon carbon and carbon heteroatom bond forming reaction on α-C of α-oxoketene-(S,S)acetals has been the chief goal of our research. This thesis will show somenew exploratory work in this field and mainly includes three aspects:
1. Copper(II) bromide catalyzed C C coupling reaction of benzylic alcohols withα-Oxo ketene-(S,S)acetals have been realized, and we have developed a convenientsynthesis of polyfunctionalized4H-chromenes and dihydrocoumarins from the easilyavailable ketene dithioacetals and2-(hydroxymethyl)phenols. The protocol iscontrolled through the choice of solvents or the reaction time and features mildreaction conditions, high yields and multifunctionality of products.
2. Pd(OAc)2catalyzed direct coupling reactions of α-oxo ketene-(S,S)acetalswith carboxylic acids in the presence of PhI(OAc)2as an oxidant has been realized,and a new synthetic method for alkenyl esters was developed. α-Alkenoyl-α-acetoxy ketene-(S,S)-acetals, products of these C O coupling reactions, are good Nazarovcyclization substances, experimental results demonstrate that the α-alkenoyl groupsignificantly affects both the reactivity and products of the Nazarov cyclization.
3. An efficient synthesis of allylic sulfones via a threee-component reactioninvolving an α-oxo ketene-(S,S)acetal, an aldehyde and4-methylbenzenesulfinicacid was developed. It is the first example of sulfonylmethylation of activatedalkenes.
引文
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