过渡金属催化的脱氢偶联反应以及基于BTA功能高分子的合成与研究
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摘要
从合成角度看发现新的化学反应能够提高原子转化率或者寻找高效且可行的方法构建复杂的有机分子是合成化学追求的目标之一,从能量角度来看合成具有功能分子的化合物,以便实现能量再生也是合成化学追求的目标之-本论文研究工作分为两部分：第一部分是过渡金属催化的C-H偶联反应,成功实现了氨化和膦化反应。第二部分主要集中于基于苯并三氮唑的共轭高分子的设计、合成以及其性质研究。
1铁催化的具有高效区域选择性的SP3胺化反应
在二价铁催化下,通过过氧叔丁醇氧化,在正癸烷的溶液里苯甲酰胺及苯磺酰胺和氮甲基吡珞烷酮发生脱氢偶联的胺化反应。对于酰胺而言,苯甲酰胺,苯磺酰胺都能和叔酰胺发生反应。酰胺上有供电子和活性高与吸电子的活性。对于叔酰胺,N-烷基环戊叔酰胺比N-烷基环基酰胺活性高。因为位阻的影响,当1-苯基吡珞烷酮以及1-环己基吡珞烷酮发生反应时产率较低。该反应属于自由基反应。另外,这种反应为以后构建C-N键提供了一种便利的方法。
2.银催化的亚磷酸二烷基酯和含缺电子基的芳基酰胺反应
一价银盐做催化剂,K2S208为氧化剂,体积比为1：1的乙腈和水的混合溶液作溶剂,实现了膦化反应。N,N-二烷基取代酰胺而言,N,N-二取代直链苯甲酰胺,N,N-二取代环状苯甲酰胺都能和亚磷酸酯发生膦化反应,得到较高的产率。对于芳基取代的N,N-二乙基苯甲酰胺而言,富电子的芳烃和缺电子芳烃都能发生膦化反应。N,N-二烷基苯磺酰胺也能发生膦化反应,得到较高产率的产物。在这条件下,N-苯基以酰胺和硝基苯都能发生反应生成产率适中的膦化产物。该反应属于自由基反应。另外,这种反应为以后构建C-P键提供了一种便利的方法。
3合成和表征基于苯并三氮唑的D-π-A共轭高分子
M1和M2,M3,M4,M5通过Sonogashira反应生成P1,P2,P3,P4基于苯并三氮唑的四个D-π-A共轭高分子,这些D-π-A的共轭高分子荧光发射范围在473-568之间。新型的合成有机高分子易溶于有机溶剂。热重分析显示该分子在320℃以下都很稳定,失重小于5%。这种理想的热性质为以后的应用提供了实际价值。从发射波长看,四个高分子的波长分别为505,473,568,528.理论计算的四个单体模型分子的能极差的高低Model-3P4>P1>P2的顺序相吻合。
From the view of synthetic chemistry, the discovery of new reactivities improve atom economy of existing processes or introduce highly effective methods to construct complex molecules is one of the long-standing goals of synthetic chemists. Synthesis of functional polymers in order to develop renewable energies is one of the long-standing goals of synthetic chemists.
This dissertation was divided into two parts. In the first section, the studies focused on transition-metal-catalyzed C-H activation methods for the synthesis of amination and Phosphonation. And in the second part, the paper mainly studied on the design, synthesis and properties of based on BTA-based D-π-A Type Copolymers.
1A highly regioselective sp3C-H amination of tertiary amides based on Fe(II) complex catalysts
When FeCl2is used as catalyst, tert-butyl hydroperoxide (TBHP) as oxidant, and n-decane as solvent, both aryl amides and aryl sulfonamides can react with N-substituted tert-amides to obtain the desired amination products. With respect to amide derivatives, both aryl amides and aryl sulfonamides can react with N-substituted tert-amides. It is found that amides involving electron-donating groups have higher reactivity than those containing electron-deficient groups. We also find that the tertiary amides, such as N-substituted cycloamides show better reaction activities than N-substituted piperidin-2-one, moderate yields could be afforded using N-ethylpyrrolidin-2-ones as material. When1-benzylpyrrolidin-2-one,1-cyclohexylpyrrolidin-2-one were chosen as substrates, only trace products were obtained owing to steric hindrance. A free radical reaction process would be involved for this reaction. It also offers a facile method for construction of C-N bonds.
2A Silver-Catalyzed Highly Regioselective Phosphonation of Arenes Bearing an Electron-Withdrawing Group
When Ag (I) compounds were chosen as catalysts, K2S2O8as oxidant and CH3CN/H2O (v:v=1:1) as solvent, the substrates bearing different N-alkyl substituent amides such as N-branched amides, cycloalkanes substituent amides were efficiently coupled to afford the expected products in high yields under the standard condition. As for aryl substituted N,N-diethylbenzamides, electron-rich group as well as most of electron-withdrawing ones on the aromatic rings were compatible in the C-P coupling reaction. N, M-dialkylbenzenesulfonamides also successfully underwent the cross-dehydrogenative-coupling (CDC) reactions with dialkyl phosphites and highly regioselective C-P bond formation was achieved with moderate to good yields. Under the identical reaction condition, both M-phenylacetamide and nitrobenzene could react with diethyl phosphonate, providing the corresponding phosphonation in moderate yields. A free radical reaction process would be involved. This facile method offers a broad scope of the construction of C-P bonds.
3Synthesis and Characterization of BTA-based D-π-A Type Copolymers
D-π-A type copolymers of P1, P2, P3and P4were synthesized via Sonogashira cross-coupling reaction of M1with M2, M3, M4and M5by using Pd(PPh3)4as a catalyst in DMF/NEt3at80℃for48h under N2, respectively. These resulting D-π-A conjugated copolymers show fluorescence emission in the range of473-568nm, The newly synthesized polymers are readily soluble in common organic solvents. the curves of TGA indicate that the polymers have relatively high thermal stability without5%weight loss before320℃, which can provide desirable thermal property for practical applications. The emissive wavelengths of four polymers are observed at505,473,568,528nm for P1, P2, P3and P4, respectively. The calculation results of model compounds show Model-3 P4> P1>P2.
1铁催化的具有高效区域选择性的SP3胺化反应
在二价铁催化下,通过过氧叔丁醇氧化,在正癸烷的溶液里苯甲酰胺及苯磺酰胺和氮甲基吡珞烷酮发生脱氢偶联的胺化反应。对于酰胺而言,苯甲酰胺,苯磺酰胺都能和叔酰胺发生反应。酰胺上有供电子和活性高与吸电子的活性。对于叔酰胺,N-烷基环戊叔酰胺比N-烷基环基酰胺活性高。因为位阻的影响,当1-苯基吡珞烷酮以及1-环己基吡珞烷酮发生反应时产率较低。该反应属于自由基反应。另外,这种反应为以后构建C-N键提供了一种便利的方法。
2.银催化的亚磷酸二烷基酯和含缺电子基的芳基酰胺反应
一价银盐做催化剂,K2S208为氧化剂,体积比为1：1的乙腈和水的混合溶液作溶剂,实现了膦化反应。N,N-二烷基取代酰胺而言,N,N-二取代直链苯甲酰胺,N,N-二取代环状苯甲酰胺都能和亚磷酸酯发生膦化反应,得到较高的产率。对于芳基取代的N,N-二乙基苯甲酰胺而言,富电子的芳烃和缺电子芳烃都能发生膦化反应。N,N-二烷基苯磺酰胺也能发生膦化反应,得到较高产率的产物。在这条件下,N-苯基以酰胺和硝基苯都能发生反应生成产率适中的膦化产物。该反应属于自由基反应。另外,这种反应为以后构建C-P键提供了一种便利的方法。
3合成和表征基于苯并三氮唑的D-π-A共轭高分子
M1和M2,M3,M4,M5通过Sonogashira反应生成P1,P2,P3,P4基于苯并三氮唑的四个D-π-A共轭高分子,这些D-π-A的共轭高分子荧光发射范围在473-568之间。新型的合成有机高分子易溶于有机溶剂。热重分析显示该分子在320℃以下都很稳定,失重小于5%。这种理想的热性质为以后的应用提供了实际价值。从发射波长看,四个高分子的波长分别为505,473,568,528.理论计算的四个单体模型分子的能极差的高低Model-3
From the view of synthetic chemistry, the discovery of new reactivities improve atom economy of existing processes or introduce highly effective methods to construct complex molecules is one of the long-standing goals of synthetic chemists. Synthesis of functional polymers in order to develop renewable energies is one of the long-standing goals of synthetic chemists.
This dissertation was divided into two parts. In the first section, the studies focused on transition-metal-catalyzed C-H activation methods for the synthesis of amination and Phosphonation. And in the second part, the paper mainly studied on the design, synthesis and properties of based on BTA-based D-π-A Type Copolymers.
1A highly regioselective sp3C-H amination of tertiary amides based on Fe(II) complex catalysts
When FeCl2is used as catalyst, tert-butyl hydroperoxide (TBHP) as oxidant, and n-decane as solvent, both aryl amides and aryl sulfonamides can react with N-substituted tert-amides to obtain the desired amination products. With respect to amide derivatives, both aryl amides and aryl sulfonamides can react with N-substituted tert-amides. It is found that amides involving electron-donating groups have higher reactivity than those containing electron-deficient groups. We also find that the tertiary amides, such as N-substituted cycloamides show better reaction activities than N-substituted piperidin-2-one, moderate yields could be afforded using N-ethylpyrrolidin-2-ones as material. When1-benzylpyrrolidin-2-one,1-cyclohexylpyrrolidin-2-one were chosen as substrates, only trace products were obtained owing to steric hindrance. A free radical reaction process would be involved for this reaction. It also offers a facile method for construction of C-N bonds.
2A Silver-Catalyzed Highly Regioselective Phosphonation of Arenes Bearing an Electron-Withdrawing Group
When Ag (I) compounds were chosen as catalysts, K2S2O8as oxidant and CH3CN/H2O (v:v=1:1) as solvent, the substrates bearing different N-alkyl substituent amides such as N-branched amides, cycloalkanes substituent amides were efficiently coupled to afford the expected products in high yields under the standard condition. As for aryl substituted N,N-diethylbenzamides, electron-rich group as well as most of electron-withdrawing ones on the aromatic rings were compatible in the C-P coupling reaction. N, M-dialkylbenzenesulfonamides also successfully underwent the cross-dehydrogenative-coupling (CDC) reactions with dialkyl phosphites and highly regioselective C-P bond formation was achieved with moderate to good yields. Under the identical reaction condition, both M-phenylacetamide and nitrobenzene could react with diethyl phosphonate, providing the corresponding phosphonation in moderate yields. A free radical reaction process would be involved. This facile method offers a broad scope of the construction of C-P bonds.
3Synthesis and Characterization of BTA-based D-π-A Type Copolymers
D-π-A type copolymers of P1, P2, P3and P4were synthesized via Sonogashira cross-coupling reaction of M1with M2, M3, M4and M5by using Pd(PPh3)4as a catalyst in DMF/NEt3at80℃for48h under N2, respectively. These resulting D-π-A conjugated copolymers show fluorescence emission in the range of473-568nm, The newly synthesized polymers are readily soluble in common organic solvents. the curves of TGA indicate that the polymers have relatively high thermal stability without5%weight loss before320℃, which can provide desirable thermal property for practical applications. The emissive wavelengths of four polymers are observed at505,473,568,528nm for P1, P2, P3and P4, respectively. The calculation results of model compounds show Model-3
引文
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