基于二硫缩烯酮中间体的钯催化碳硫键活化新交叉偶联反应研究
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摘要
过渡金属催化的碳硫键断裂，形成碳碳键及碳杂原子键是交叉偶联方法学研究领域的重要课题。许多有机硫化物已被成功地应用于该类转化中。同偶联反应中普遍使用的传统有机卤化物偶联体相比较，有机硫化物种类繁多，往往具有更好的稳定性，且易于制备。因此，开发有机硫偶联体，尤其是结构多样的有机硫化物，在交叉偶联反应中的应用，不但具有经济方面的优势，更可预期新型成键模式的发现，对过渡金属催化的交叉偶联反应及应用研究具有十分重要的意义。
二硫缩烯酮是一类多官能团有机中间体，其结构多样、易于制备，已被广泛用于合成各种碳环及杂环化合物。α-羰基二硫缩烯酮可以看作是一类特殊的官能化硫醚，同时又具有插烯型硫酯的结构特征。鉴于其分子结构的多样性和反应特性，我们创造性地将二硫缩烯酮发展为新型有机硫偶联体，探索了基于过渡金属催化下的碳硫键活化及转化反应，建立了系列高效的碳碳成键新方法。本论文的主要研究内容如下：
1、以铜盐为辅助试剂，实现了钯催化下，α-羰基二硫缩烯酮与硼酸的去硫碳碳偶联反应，简单高效地制备了四取代烯类化合物。该反应条件温和，可在中性介质中进行。
2、以铜盐为辅助试剂，实现了钯催化下，2-烷硫基-3-酯基苯并呋喃与邻羟基苯硼酸的去硫碳碳偶联继而环合反应，合成了系列具有潜在生物活性的Coumestan衍生物,为植物雌激素类天然产物的合成提供了有效方法。
3、实现了铜催化的α,α-双羰基二硫缩烯酮与硼酸的偶联，合成了四取代烯类化合物。实际上，这是首次实现的铜盐催化下简单硫酯类似物与硼酸的偶联，从而进一步拓展了去硫偶联反应的应用。
4、实现了钯催化下，α-酰胺基二硫缩烯酮与苯炔的[4+2]环合反应。反应历经二硫缩烯酮碳硫键活化、与苯炔分子间碳碳键偶联以及分子内碳氮偶联过程，构筑了喹啉酮类物质。在反应体系中，钯存在下，二硫缩烯酮的碳硫键活化成为主导反应，硫原子对苯炔的加成反应受到抑制，二硫缩烯酮表现出了很好的化学选择性。实际上该部分工作首次实现了基于碳硫键活化的苯炔环加成反应，提供了一种高效制备多官能化喹啉酮衍生物的新方法。
In the area of transition metal-catalyzed cross-coupling reactions, the C-S bondcleaving reaction have attracted a lot of attention in the last decade as they provide agood alternative to the use of organo-halide reagents in traditional cross-couplingreactions. As compared to the corresponding halides, thioorganic derivative aretantalizing alternatives due to their diversity and stability. The availability of a widerange of organosulfur species provides the opportunity for developing inexpensivesubstrates and novel transformations for the synthesis of interesting organiccompounds.
Easily prepared multiple functional ketene dithioacetals serves as buildingblocks for the construction of polysubstituted carbo-and heterocyclic compounds.From the point of structure, α-oxo ketene-(S,S)acetals can be seemed as eitherfunctional thioether, or vinylogous ester. Owing to these chemical properties, wecreatively developed ketene dithioacetals to as novel electrophilic organosulfurcoupling partners, studied transition metal catalyzed C-C bond formations through theC-S bond cleavages. This thesis mainly includes five aspects:
1. Palladium-catalyzed, copper-mediated desulfitative crossing-couplingbetween ketene dithioacetals and boronic acids have been studied. A convenientsynthesis of tetrasubstituted olefins under neutral conditions have been realized.
2. Palladium-catalyzed, copper-mediated C S activation for [3+3] annulationof2(methylthio)benzofuran-3-carboxylates and2hydroxyphenylboronic acids havebeen realized. This method allows new approach to a class of coumestan derivatives,which possess potential biological properties and estrogenic activity.
3. Copper-catalyzed C C coupling reaction of α,α-dioxo ketene-(S,S)acetals andboronic acids to provide tetrasubstituted olefins have been realized. Actually, this isthe first example of Cu-catalyzed coupling of ordinary ester with boronic acids, andexpands the spectrum of desulfitative crossing-coupling.
4. Catalyzed by Pd(OAc)2, a wide range of α-carbamoyl ketene dithioacetalsreadily react with arynes afford functionalized2-quinolinones to selectively in highyields under neutral reaction conditions by a C-S activation/aryneinsertion/intramolecular coupling sequence. The insertion of an aryne into a C-S bondcan suppress the addition of an S nucleophile to the aryne in the presence ofpalladium. This process represents the first example for the reaction of arynes with thioorganics based on palladium-catalyzed C-S bond activation. A novel and efficientprotocol for the synthesis of functionalized2-quinolinone has been achieved.
二硫缩烯酮是一类多官能团有机中间体，其结构多样、易于制备，已被广泛用于合成各种碳环及杂环化合物。α-羰基二硫缩烯酮可以看作是一类特殊的官能化硫醚，同时又具有插烯型硫酯的结构特征。鉴于其分子结构的多样性和反应特性，我们创造性地将二硫缩烯酮发展为新型有机硫偶联体，探索了基于过渡金属催化下的碳硫键活化及转化反应，建立了系列高效的碳碳成键新方法。本论文的主要研究内容如下：
1、以铜盐为辅助试剂，实现了钯催化下，α-羰基二硫缩烯酮与硼酸的去硫碳碳偶联反应，简单高效地制备了四取代烯类化合物。该反应条件温和，可在中性介质中进行。
2、以铜盐为辅助试剂，实现了钯催化下，2-烷硫基-3-酯基苯并呋喃与邻羟基苯硼酸的去硫碳碳偶联继而环合反应，合成了系列具有潜在生物活性的Coumestan衍生物,为植物雌激素类天然产物的合成提供了有效方法。
3、实现了铜催化的α,α-双羰基二硫缩烯酮与硼酸的偶联，合成了四取代烯类化合物。实际上，这是首次实现的铜盐催化下简单硫酯类似物与硼酸的偶联，从而进一步拓展了去硫偶联反应的应用。
4、实现了钯催化下，α-酰胺基二硫缩烯酮与苯炔的[4+2]环合反应。反应历经二硫缩烯酮碳硫键活化、与苯炔分子间碳碳键偶联以及分子内碳氮偶联过程，构筑了喹啉酮类物质。在反应体系中，钯存在下，二硫缩烯酮的碳硫键活化成为主导反应，硫原子对苯炔的加成反应受到抑制，二硫缩烯酮表现出了很好的化学选择性。实际上该部分工作首次实现了基于碳硫键活化的苯炔环加成反应，提供了一种高效制备多官能化喹啉酮衍生物的新方法。
In the area of transition metal-catalyzed cross-coupling reactions, the C-S bondcleaving reaction have attracted a lot of attention in the last decade as they provide agood alternative to the use of organo-halide reagents in traditional cross-couplingreactions. As compared to the corresponding halides, thioorganic derivative aretantalizing alternatives due to their diversity and stability. The availability of a widerange of organosulfur species provides the opportunity for developing inexpensivesubstrates and novel transformations for the synthesis of interesting organiccompounds.
Easily prepared multiple functional ketene dithioacetals serves as buildingblocks for the construction of polysubstituted carbo-and heterocyclic compounds.From the point of structure, α-oxo ketene-(S,S)acetals can be seemed as eitherfunctional thioether, or vinylogous ester. Owing to these chemical properties, wecreatively developed ketene dithioacetals to as novel electrophilic organosulfurcoupling partners, studied transition metal catalyzed C-C bond formations through theC-S bond cleavages. This thesis mainly includes five aspects:
1. Palladium-catalyzed, copper-mediated desulfitative crossing-couplingbetween ketene dithioacetals and boronic acids have been studied. A convenientsynthesis of tetrasubstituted olefins under neutral conditions have been realized.
2. Palladium-catalyzed, copper-mediated C S activation for [3+3] annulationof2(methylthio)benzofuran-3-carboxylates and2hydroxyphenylboronic acids havebeen realized. This method allows new approach to a class of coumestan derivatives,which possess potential biological properties and estrogenic activity.
3. Copper-catalyzed C C coupling reaction of α,α-dioxo ketene-(S,S)acetals andboronic acids to provide tetrasubstituted olefins have been realized. Actually, this isthe first example of Cu-catalyzed coupling of ordinary ester with boronic acids, andexpands the spectrum of desulfitative crossing-coupling.
4. Catalyzed by Pd(OAc)2, a wide range of α-carbamoyl ketene dithioacetalsreadily react with arynes afford functionalized2-quinolinones to selectively in highyields under neutral reaction conditions by a C-S activation/aryneinsertion/intramolecular coupling sequence. The insertion of an aryne into a C-S bondcan suppress the addition of an S nucleophile to the aryne in the presence ofpalladium. This process represents the first example for the reaction of arynes with thioorganics based on palladium-catalyzed C-S bond activation. A novel and efficientprotocol for the synthesis of functionalized2-quinolinone has been achieved.
引文
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