基于α-硫代羰基底物的炔硫醚的一锅合成方法研究
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摘要
炔硫醚在有机合成、单分子膜自组装以及纳米自组装等方面具有重要地位。因此探索新的合成炔硫醚的方法有着非常重要的理论和实际意义。一锅合成法是一种资源节约和环境友好的方法，它具有操作简化、总产率较高以及经济节省等特点，很受研究者的青睐。本文在实验室前期研究工作的基础上，以消除反应为基本反应，着重从方法学角度考察了各种α-硫代羰基化合物为底物，“一锅三步”制备炔硫醚的合成战略。本文大致可以分为两个部分：第一部分主要介绍炔硫醚(芳炔硫醚、二(芳乙炔)硫醚、(4-芳基-1,3-丁二炔)硫醚和共轭烯炔硫醚)的一锅合成方法研究；第二部分以苯基芳乙炔硫醚为例介绍了炔硫醚在[3+2]环加成中的应用。
本文首次比较系统地研究了各种α-硫代芳基乙酮(51a—k，52a—k，71a—k)为底物制备芳乙炔硫醚(53a—k，54a—k，72a—k)的“一锅三步”反应。试剂分三个阶段加入：i)碱；ii) ClP(O)(OEt)2；iii)碱。论文考察了四类碱(BuLi、LiHMDS、LDA和t-BuOK)对“一锅反应”的影响，结果表明第一阶段碱的使用对芳乙炔硫醚的合成影响很大，直接决定其反应历程；通过对磷酸烯醇酯中间体的捕捉、结构分析，以及该中间体在LiHMDS下的消除反应，验证了“一锅反应”机理的合理性：包括亲核取代和消除等基本反应，经历了碳负离子和烯醇负离子的互变异构结构，最终消除一分子磷酸二乙酯得到各种芳乙炔硫醚。与过去的双消除相比，“一锅三步”反应的优点一方面表现在整个反应过程中，只需使用一种底物，反应试剂分三个阶段加入，操作上更加简便；另一方面，与硫原子连接的基团容易扩展，可以是烷基、芳基等取代基。此外，底物的制备简单，由廉价易得的芳基乙酮为起始原料，依次通过溴化和亲核取代反应高产率获得。
本文首次提出了以二(芳甲酰甲基)硫醚(91a—h)为底物的二(芳乙炔)硫醚(92a—h)的一锅合成策略，考察了BuLi和LiHMDS对“一锅反应”的影响；成功获得了二(芳乙炔)硫醚92h的适合X-射线单晶衍射分析的晶体，并对其进行了晶体结构分析。
本文首次提出了以4-烃硫基-1-芳基-1,3-丁二酮(101a—e，102a—e，103a—e)为底物的(4-芳基-1,3-丁二炔)硫醚(104a—e，105a—e，106a—e)的一锅合成策略；通过1H NMR分析考察了原料和底物在CDCl3中酮式和烯醇式结构的比例关系；将“一锅三步”合成策略与甲基(4-芳基-1,3-丁二炔)硫醚的双消除一锅合成方法进行了比较。底物(4-烃硫基-1-芳基-1,3-丁二酮)是以芳基乙酮为起始原料，依次经缩合、溴化和亲核取代反应制得。
本文以芳香醛为起始原料，依次经羟醛缩合、溴化和亲核取代反应获得了一种新的底物4-烃硫基-1-芳基-1-丁烯-3-酮(131a—e，132a—e，133a—e)，首次提出了基于该底物的共轭烯炔硫醚(134a—e，135a—e，136a—e)的一锅合成策略，对一锅反应产物的构型通过空间排斥作用进行了推测。
本文以苯基芳乙炔硫醚为例，将炔硫醚应用于[3+2]环加成反应，首次在三唑上导入含硫的基团，得到两种互为异构体的1-苄基-4-芳基-5-苯硫基-1,2,3-三唑(147a—b，148d—h)和1-苄基-5-芳基-4-苯硫基-1,2,3-三唑(148a—b，148d—h)，均为新化合物；成功获得三唑147a和148a的适合X-射线单晶衍射分析的晶体，对其进行了晶体结构分析，确定了两种异构体的构型；对其反应机理进行了推测。
本文以消除反应为基本反应，通过合成路线设定，碱对反应的影响及中间体捕捉和分析，提出了基于-硫代羰基底物的各种炔硫醚的一锅合成思想。这种为炔硫醚的合成提供的新的方法学研究，不仅丰富了有机化学内容，对于炔硫醚在纳米自组装的应用也具有重要意义。本文共制得71个炔硫醚化合物，其中有54个是新化合物。所有原料都经过了1HNMR测定得到了确认，所有炔硫醚以及三唑化合物都经过了1HNMR、13CNMR、IR、MS和HRMS表征得到确认。
Ethynyl sulfides are very important intermediates in organic synthesis and can be used asversatile building blocks for a variety of chemical purposes. So it is academic and practicalsignificance to explore new methods for preparing ethynyl sulfides. The one-pot procedure,which has the advantage of simplified process, higher total yield and economical operation, isa resource-saving and environment friendly methodology and has long been an attractive areaof research. On the basis of the previous work of our lab, one-pot three-step strategy forpreparing ethynyl sulfides by-thio carbonyl compounds as substrates was developed. Mystudy can be divided into two parts entirely: the one-pot synthetic protocol of ethynyl sulfides(including arylethynyl sulfides, bis(arylethynyl) sulfides, aryl diyne sulfides and conjugatedenyne sulfides) was described in the first part; the application of ethynyl sulfides in [3+2]cycloaddition reaction was discussed in the second part.
The one-pot three-step procedure for preparing arylethynyl sulfides (53a—k,54a—k,72a—k) by-thio aryl ethanone (51a—k,52a—k,71a—k) as substrates was presented forthe first time. The reagents were added to the solution of the substrates in THF sequentially asfollows: i) base; ii) ClP(O)(OEt)2; iii) base. BuLi, LiHMDS, LDA and t-BuOK werediscussed in one-pot reaction. The results showed the use of the base in the first stageinfluenced on the synthesis of arylethynyl sulfides greatly and decided the mechanism of thereaction. To obtain insight into the mechanism of this one-pot reaction, we attempted toisolate enol phosphate intermediates. A differentiated two-step procedure was performed toprove the formation of enol phosphate. The results from the1H and31P NMR spectroscopicdata reveal that the intermediate was formed in a Z/E mixture. And the Z-configuration ofmajor isomer has also been confirmed by NOESY experiment. Furthermore, we investigatedthe elimination reaction of enol phosphate intermediates, which, upon treatment theintermediates in THF with LiHMDS, occurred smoothly to provide arylethynyl sulfides.Therefore, on the basis of this evidence, we can conclude that the mechanism involves theformation of an enol phosphate and a subsequent base-induced elimination. Compared withthe double elimination mentioned, the advantage of the one-pot three-step protocol use onlyone substrate and the reagent just can be added in three stages into the system, the operationbecomes more conveniently. Additionally, the substrates can be obtained easily from arylehtanone through bromination and nucleophilic substitute reaction.
The one-pot procedure for bis(arylethynyl) sulfides (92a—h) by substrates bis(arylethanonyl) sulfides (91a—h) as substrates was presented. BuLi and LiHMDS wereexamined in one-pot reaction.92h was characterized by X-ray single crystal diffraction.
The one-pot procedure for aryl diyne sulfides (104a—e,105a—e and106a—e) by4-(alkylthio)-1-arylbutane-1,3-dione (101a—e,102a—e and103a—e) as substrates wasdiscussed. The ration of β-diketo and enol structures of the materials107a—h and thesubstrates in CDCl3was investigated by1H NMR. The comparation of the method to preparearyl diyne sulfides between the one-pot three-step protocol and the double elimination one-potprotocol was employed. The substrate can be obtained from aryl ethanone via condensation,bromination and nucleophilic substitute reaction.
The preparation of conjugated enyne sulfides (134a—e,135a—e,136a—e) via one-potprocedure by-thio aryl substrates (131a—e,132a—e,133a—e) was described for the firsttime. The substrates can be obtained from aryl aldehydes via aldol condensatioon,bromination and nucleophilic substitute reaction. And the configuration of conjugated enynesulfides was postulated by the steic effect.
The [3+2] cycloaddition reaction between phenyl ethynyl sulfides and benzyl azide wasdescribed and triazoles ((147a—b,147d—h) and148a—b,148d—h) were obtained.147aand148a were characterized by X-ray single crystal diffraction and the configuration wasdecided. The probable mechanism was postulated.
In the dissertation, the idea of the one-pot three-step protocol to prepare ethynyl sulfidesby-thio carbonyl compounds as substrates was discussed by designing synthesis route,choosing appropriate base, capturing and identifying the intermediates. The one-pot procedurewill enrich the content of organic chemisty and it is significance of the application inself-assembled monolayers and related fields. All materials were characterized by1H NMR.All ethynyl sulfides and the triazoles were identified by1H NMR,13C NMR, IR, MS andHRMS.
本文首次比较系统地研究了各种α-硫代芳基乙酮(51a—k，52a—k，71a—k)为底物制备芳乙炔硫醚(53a—k，54a—k，72a—k)的“一锅三步”反应。试剂分三个阶段加入：i)碱；ii) ClP(O)(OEt)2；iii)碱。论文考察了四类碱(BuLi、LiHMDS、LDA和t-BuOK)对“一锅反应”的影响，结果表明第一阶段碱的使用对芳乙炔硫醚的合成影响很大，直接决定其反应历程；通过对磷酸烯醇酯中间体的捕捉、结构分析，以及该中间体在LiHMDS下的消除反应，验证了“一锅反应”机理的合理性：包括亲核取代和消除等基本反应，经历了碳负离子和烯醇负离子的互变异构结构，最终消除一分子磷酸二乙酯得到各种芳乙炔硫醚。与过去的双消除相比，“一锅三步”反应的优点一方面表现在整个反应过程中，只需使用一种底物，反应试剂分三个阶段加入，操作上更加简便；另一方面，与硫原子连接的基团容易扩展，可以是烷基、芳基等取代基。此外，底物的制备简单，由廉价易得的芳基乙酮为起始原料，依次通过溴化和亲核取代反应高产率获得。
本文首次提出了以二(芳甲酰甲基)硫醚(91a—h)为底物的二(芳乙炔)硫醚(92a—h)的一锅合成策略，考察了BuLi和LiHMDS对“一锅反应”的影响；成功获得了二(芳乙炔)硫醚92h的适合X-射线单晶衍射分析的晶体，并对其进行了晶体结构分析。
本文首次提出了以4-烃硫基-1-芳基-1,3-丁二酮(101a—e，102a—e，103a—e)为底物的(4-芳基-1,3-丁二炔)硫醚(104a—e，105a—e，106a—e)的一锅合成策略；通过1H NMR分析考察了原料和底物在CDCl3中酮式和烯醇式结构的比例关系；将“一锅三步”合成策略与甲基(4-芳基-1,3-丁二炔)硫醚的双消除一锅合成方法进行了比较。底物(4-烃硫基-1-芳基-1,3-丁二酮)是以芳基乙酮为起始原料，依次经缩合、溴化和亲核取代反应制得。
本文以芳香醛为起始原料，依次经羟醛缩合、溴化和亲核取代反应获得了一种新的底物4-烃硫基-1-芳基-1-丁烯-3-酮(131a—e，132a—e，133a—e)，首次提出了基于该底物的共轭烯炔硫醚(134a—e，135a—e，136a—e)的一锅合成策略，对一锅反应产物的构型通过空间排斥作用进行了推测。
本文以苯基芳乙炔硫醚为例，将炔硫醚应用于[3+2]环加成反应，首次在三唑上导入含硫的基团，得到两种互为异构体的1-苄基-4-芳基-5-苯硫基-1,2,3-三唑(147a—b，148d—h)和1-苄基-5-芳基-4-苯硫基-1,2,3-三唑(148a—b，148d—h)，均为新化合物；成功获得三唑147a和148a的适合X-射线单晶衍射分析的晶体，对其进行了晶体结构分析，确定了两种异构体的构型；对其反应机理进行了推测。
本文以消除反应为基本反应，通过合成路线设定，碱对反应的影响及中间体捕捉和分析，提出了基于-硫代羰基底物的各种炔硫醚的一锅合成思想。这种为炔硫醚的合成提供的新的方法学研究，不仅丰富了有机化学内容，对于炔硫醚在纳米自组装的应用也具有重要意义。本文共制得71个炔硫醚化合物，其中有54个是新化合物。所有原料都经过了1HNMR测定得到了确认，所有炔硫醚以及三唑化合物都经过了1HNMR、13CNMR、IR、MS和HRMS表征得到确认。
Ethynyl sulfides are very important intermediates in organic synthesis and can be used asversatile building blocks for a variety of chemical purposes. So it is academic and practicalsignificance to explore new methods for preparing ethynyl sulfides. The one-pot procedure,which has the advantage of simplified process, higher total yield and economical operation, isa resource-saving and environment friendly methodology and has long been an attractive areaof research. On the basis of the previous work of our lab, one-pot three-step strategy forpreparing ethynyl sulfides by-thio carbonyl compounds as substrates was developed. Mystudy can be divided into two parts entirely: the one-pot synthetic protocol of ethynyl sulfides(including arylethynyl sulfides, bis(arylethynyl) sulfides, aryl diyne sulfides and conjugatedenyne sulfides) was described in the first part; the application of ethynyl sulfides in [3+2]cycloaddition reaction was discussed in the second part.
The one-pot three-step procedure for preparing arylethynyl sulfides (53a—k,54a—k,72a—k) by-thio aryl ethanone (51a—k,52a—k,71a—k) as substrates was presented forthe first time. The reagents were added to the solution of the substrates in THF sequentially asfollows: i) base; ii) ClP(O)(OEt)2; iii) base. BuLi, LiHMDS, LDA and t-BuOK werediscussed in one-pot reaction. The results showed the use of the base in the first stageinfluenced on the synthesis of arylethynyl sulfides greatly and decided the mechanism of thereaction. To obtain insight into the mechanism of this one-pot reaction, we attempted toisolate enol phosphate intermediates. A differentiated two-step procedure was performed toprove the formation of enol phosphate. The results from the1H and31P NMR spectroscopicdata reveal that the intermediate was formed in a Z/E mixture. And the Z-configuration ofmajor isomer has also been confirmed by NOESY experiment. Furthermore, we investigatedthe elimination reaction of enol phosphate intermediates, which, upon treatment theintermediates in THF with LiHMDS, occurred smoothly to provide arylethynyl sulfides.Therefore, on the basis of this evidence, we can conclude that the mechanism involves theformation of an enol phosphate and a subsequent base-induced elimination. Compared withthe double elimination mentioned, the advantage of the one-pot three-step protocol use onlyone substrate and the reagent just can be added in three stages into the system, the operationbecomes more conveniently. Additionally, the substrates can be obtained easily from arylehtanone through bromination and nucleophilic substitute reaction.
The one-pot procedure for bis(arylethynyl) sulfides (92a—h) by substrates bis(arylethanonyl) sulfides (91a—h) as substrates was presented. BuLi and LiHMDS wereexamined in one-pot reaction.92h was characterized by X-ray single crystal diffraction.
The one-pot procedure for aryl diyne sulfides (104a—e,105a—e and106a—e) by4-(alkylthio)-1-arylbutane-1,3-dione (101a—e,102a—e and103a—e) as substrates wasdiscussed. The ration of β-diketo and enol structures of the materials107a—h and thesubstrates in CDCl3was investigated by1H NMR. The comparation of the method to preparearyl diyne sulfides between the one-pot three-step protocol and the double elimination one-potprotocol was employed. The substrate can be obtained from aryl ethanone via condensation,bromination and nucleophilic substitute reaction.
The preparation of conjugated enyne sulfides (134a—e,135a—e,136a—e) via one-potprocedure by-thio aryl substrates (131a—e,132a—e,133a—e) was described for the firsttime. The substrates can be obtained from aryl aldehydes via aldol condensatioon,bromination and nucleophilic substitute reaction. And the configuration of conjugated enynesulfides was postulated by the steic effect.
The [3+2] cycloaddition reaction between phenyl ethynyl sulfides and benzyl azide wasdescribed and triazoles ((147a—b,147d—h) and148a—b,148d—h) were obtained.147aand148a were characterized by X-ray single crystal diffraction and the configuration wasdecided. The probable mechanism was postulated.
In the dissertation, the idea of the one-pot three-step protocol to prepare ethynyl sulfidesby-thio carbonyl compounds as substrates was discussed by designing synthesis route,choosing appropriate base, capturing and identifying the intermediates. The one-pot procedurewill enrich the content of organic chemisty and it is significance of the application inself-assembled monolayers and related fields. All materials were characterized by1H NMR.All ethynyl sulfides and the triazoles were identified by1H NMR,13C NMR, IR, MS andHRMS.
引文
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