耐水抗氧型有机金属路易斯酸的设计、合成与催化应用研究
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摘要
有机金属路易斯酸在现代有机化工中具有重要作用。在过去二十年里,这一领域得到了深入发展。新型路易斯酸催化研究需要设计合成更高催化活性、更高选择性、更广反应适用性、更稳定、廉价和绿色的有机金属路易斯酸催化剂。目前已有的有机金属路易斯酸催化剂主要存在以下问题：(1)部分有机金属配合物的稳定性差、酸性弱、催化活性低和选择性差；(2)配合物中的强路易斯酸性与高稳定性难以兼得；(3)催化剂本身毒性大或者催化体系对环境不友好；(4)所用金属价格相对昂贵；(5)只对特定的几个反应具有催化活性,不能广泛应用到多种反应类型。在绿色化学和可持续发展的影响下,如何设计合成出高效、廉价、稳定、广谱的绿色路易斯酸是目前有机金属路易斯酸化学中的关键科学问题。
本文针对有机金属路易斯酸存在的不足以及茂金属配合物和有机铋、锑配合物的特点,提出构建稳定的碳-金属键的同时,引入强拉电子能力的阴离子,设计合成了30余种耐水抗氧型有机金属路易斯酸催化剂,并采用NMR、X射线单晶衍射、TG-DSC等多种表征技术对有机金属路易斯酸配合物的组成、结构和物化性质进行了分析表征,还探讨了其在碳-杂键和碳-碳键形成反应等有机化工中具有重要作用有机反应中的催化应用,主要研究结果和结论如下：
1)采用具有稳定C-M键的茂金属氯化物Cp2MCl2(M=Zr (1a)、Hf(1b)、Ti(1c)),通过引入强拉电子能力的全氟烷基或芳基磺酸基团,构建了耐水抗氧型路易斯酸双核茂锆、茂铪路易斯酸配合物[(CpZr(OH2)3)2(μ2-OH)2][C6F5SO3]4·6H2(2a·6H2O)、[(CpHf(OH2)3)2(μ2-OH)2][OSO2C8F17]4·4H2O·2THF (2b·4H2O·2THF)]和单核茂锆、茂钛全氟烷基磺酸配合物Cp2M(OSO2C8F17)2·nH2O·THF (M=Zr (3a·3H2O·THF), Ti3b·(2H2O·THF))、 Cp2M(OSO2C4F9)2·nH2O (M=Zr (3c·2H2O), Ti (3d·2H2O))。实验表明,这6种配合物均为耐水抗氧的离子型茂金属配合物,金属与环戊二烯基形成稳定的碳-金属键,阴离子与金属的配位水分子形成氢键团簇在阳离子金属中心周围,从而产生耐水抗氧性能。这些配合物易溶于极性溶剂且具有与Sc(OTf)3相当的强酸性,能够催化如碳-碳键形成等有机合成反应。基于这些茂金属全氟磺酸配合物,开发了一种醇、酚、硫醇和胺的通用酰化方法,并可应用于生物柴油的合成。基于Cp2Zr(OSO2C8F17)2催化糖基化反应开发了葡萄糖骨架的生物活性分子合成法。基于Cp2Ti(OSO2C8F17)2/Zn粉催化体系,开发了硫(硒)代酯、α-硫(硒)代羰基化合物以及单硫(硒)醚化合物的简易绿色合成法。另外,还发现这些配合物为烯丙基化反应,Mukaiyama-aldol反应,Friedel-Crafts酰化反应,Mannich反应和酮自缩合芳构化反应等碳-碳键形成反应的高效催化剂。综上所述,本文成功合成了具有强酸性的耐水抗氧型茂金属全氟磺酸配合物,并可作为一种高效广谱的C-C键和C-Z(O, N, S, Se)键等成键反应的路易斯酸催化剂,在有机合成中具有广阔潜在应用前景。
2)合成了具有氮原子桥连的pincer配体4a-4c,构建了具有稳定的C-Bi键的氮原子桥连有机铋氯化物RN(C6H4CH2)2BiCl (R=tBu (5a), c-C6H11(5b), Ph (5c)),通过用强拉电子能力的阴离子置换其中的氯原子,构建了耐水抗氧型有机铋配合物路易斯酸催化剂c-C6H11N(C6H4CH2)2BiX (X=BF4(6a), OSO2CgF17(6b)),这些催化剂在烯丙基化反应和Mannich反应中表现出与过渡金属路易斯酸相当的优异催化性能。通过氧原子和硫原子桥连合成了双核的有机铋配合物[RN(C6H4CH2)2Bi]2X (X=O, R=tBu (8a), c-C6H11(8b), Ph (8c); X=S, R=tBu (9a), c-C6H11(9b), Ph (9c))。与单核的tBuN(C6H4CH2)2BiOMe (7a)和5a-5c相比,这类配合物在二氧化碳和环氧化物合成环状碳酸酯的催化反应中表现出明显的双金属协同催化效应。
3)合成了具有路易斯碱位的硫桥pincer配体4d,构建具有稳定的C-Bi键的硫桥有机铋氯化物S(C6H4CH2)2BiCl (5d),通过用强拉电子能力的阴离子置换其中的氯原子,构建了耐水抗氧型路易斯酸碱双功能催化剂S(C6H4CH2)2Bi(OH2)X (X=ClO4(10a), BF4(10b), OSO2C4F9(10c), OSO2CgF17(10d))。这类催化剂在直接非对映异构选择性Mannich反应和(E)-α,β-不饱和酮的绿色立体专一性合成反应中表现出很高的催化活性和立体选择性。基于这一绿色催化体系,开发了反应控制的自分离催化体系,实现了催化剂和产物的自动分离。另外还阐述了配合物结构与催化活性之间的构-效关系。总之,通过引入硫原子代替氮原子,极大的改善了有机铋配合物的催化活性和立体选择性,构建了对空气稳定的有机铋路易斯酸、碱双功能催化剂。
4)采用相同的配体4a-4c构建5,6,7,12-四氢二苯并[c,f][1,5]氮锑辛烯骨架,构建了对空气稳定的有机锑氯化物RN(C6H4CH2)2SbCl (R=tBu (11a), c-C6H11(11b), Ph(11c)),通过调变其中的对应阴离子,获得了具有较强路易斯酸性的有机锑配合物(RN(C6H4CH2)2BiX, R=c-C6H11, X=OSO2CF3(12a); R=Ph, BF4(12b), F (12c), Br (12d), I(12e)),并且发现有机锑配合物路易斯酸12a和12c在Mannich反应和环氧化物的胺解反应中表现出了很好的催化活性和立体选择性,这说明通过调变N-Sb键的键强可以调变配位原子的配位能力,使得参与配位的氮原子上的孤对电子可以同时作为路易斯碱中心,可被认为是不自我淬灭的路易斯酸碱对。另外,通过氧原子桥连合成了双核有机锑配合物[(?)N(C6H4CH2)2Sb]2O (R=tBu (14a), c-C6H11(14b),Ph(14c))。与单核的(13a)和11a-11c相比,这类配合物在二氧化碳和环氧化物合成环状碳酸酯的催化反应中表现出明显的双金属协同催化效应。
Organometallic Lewis acid plays an important role in modern organic synthesis. During the past two decades the uninterrupted expansion of this field has continued. New Lewis acid research is targeting more versatile, more selective, more reactive, more stable, cheaper, and greener catalysts. Up to now, the development of organometallic Lewis acid has suffered from several shortcomings:(1) Partial organometallic Lewis acids are air-or moisture-sensitive, lower Lewis acidic, poor catalytic active and selective catalyst;(2) It is hard to achieve both properties of strong Lewis acidity and high stability in a same Lewis catalytic system;(3) The Lewis acid catalyst is high toxic or catalytic system is not environmental-friendly;(4) The metal adopted in some of organometallic complexes are too expansive to use in wide application;(5) most of organometallic Lewis acids are not versatile for many kinds of reactions. With the emphasized on the "green" and "sustainable" chemistry, how to design and synthesis of high catalytic efficient, cheaper, stable and versatile green organometallic Lewis acid is the key issue in modern organometallic Lewis acid catalysis chemistry.
Based on the shortcomings of the organometallic Lewis acid chemistry and metallocence and organobismuth and organoantimony special features, by construction of stable C-M bond and incorporation of larger electronic-withdrawing group, a serial of air-stable, water-tolerant organometallic Lewis acid catalysts were synthesized and characterized by NMR, X-ray single crystal diffraction and TG-DSC technologies, etc to demonstrate their composition, structure and physical or chemical properties. Moreover, their applications in construction of carbon-heteroatom and carbon-carbon bond formation were also investigated. Some innovative results and conclusions were obtained as follows:
1) By incorporation of larger electronic-withdrawing long chain perfluoroalkyl group ion to place the chloride in Cp2MCl2(M=Zr (1a)、Hf (1b)、Ti (1c)), air-stable and water-tolerant metallocene complex Lewis acid catalysts ([(CpZr(OH2)3)2(μ2-OH)2][C6F5SO3]4·6H2O (2a·6H2O),[(CpHf(OH2)3)2(μ2-OH)2][OSO2C8F17]4·4H2O·2THF (2b·4H2O·2THF)},Cp2M(OSO2C8F17)2·nH2O·THF (M=Zr (3a·3H2O·THF), Ti3b·(2H2O·THF)) and Cp2M(OSO2C4F9)2·nH2O (M=Zr (3c·2H2O), Ti (3d·2H2O))) were synthesized. These complexes can be stable in the open air for a month or a year and remain as dry crystal or white powders. The anions are packed around the complex cation in such a way that their oxygen atoms point towards the H2O ligands.
The perfluoroalkyl group sides of the anion, on the other hand, are clustered together to form the hydrophobic domains. These complexes showed heat resistant and high solubility in polar organic solvent. Furthermore, they also showed high Lewis acidity in the same level as that of Sc(OTf)3, which can be used to promote carbon-carbon bond formation. Based on these complexes, we developed a versatile acylation method for alcohol, phenol, thiol and amine, which can be applied in biodiesel synthesis. Cp2Zr(OSO2C8F17)2can be also used in glycosylation to prepare bioactive molecules. Based on the Cp2Ti(OSO2CgF17)2/Zn dust catalytic system, we developed a simple, efficient and green synthetic method to prepare thio(seleno)ester, a-thio(seleno)carbonyl compounds and thio(seleno)ether. These metallocene Lewis acid catalysts also showed high catalytic efficient in allylation, Mukaiyama-aldol reaction, Friedel-Crafts acylation, Mannich reaction, and cyclotrimerization of ketones. In a word, the metallocene complexes can be used as versatile organometallic Lewis acid catalyst in various carbon-carbon bond and carbon-heteroatom formation reactions. On account of its stability, storability, and versatile ability, these complexes should find broad catalytic applications in organic synthesis.
2) By design and synthesis of nitrogen-bridged ligands (4a-4c), the organobismuth chlorides RN(C6H4CH2)2BiCl (R=tBu (5a), c-C6H11(5b), Ph (5c)) with stable C-Bi bonds were synthesized. By incorporation of larger electronic-withdrawing counter anion to replace the chloride, air-stable and water-tolerant organobismuth complex Lewis acids c-C6H11N(C6H4CH2)2BiX (X=BF4(6a), OSO2C8F17(6b)) were synthesized. They showed high air-stability and Lewis acidity as well as heat resistant and can be applied as catalyst in Mannich reaction and allylation reaction. While the binuclear organobismuth complexes bridged by sulfur or oxygen atoms ([RN(C6H4CH2)2Bi]2X (X=O, R=tBu (8a), c-C6H11(8b), Ph(8c); X=S, R=tBu (9a), c-C6H11(9b), Ph (9c))) showed bimetallic cooperative catalytic activity in cyclic carbonate synthesis from epoxide and CO2compared with tBuN(C6H4CH2)2BiOMe (7a) and5a-5c.
3) By adopting sulfur bridged pincer ligand (4d) with suitable Lewis basic site, an organobismuth chloride (5d) bearing stable C-Bi bonds was synthesized. By incorporation of larger electronic-withdrawing counter anion to place the chloride, air-stable and water-tolerant sulfur bridged organobismuth complex Lewis acids S(C6H4CH2)2Bi(OH2)X (X=ClO4(10a), BF4(10b), OSO2C4F9(10c), OSO2C8F17(10d)) were synthesized. With the exposed bismuth center acting as Lewis acid site and the uncoordinated lone pair electrons of sulfur as Lewis base site, the cationic organobismuth complexes work as bifunctional Lewis acid/base catalysts. These complexes showed high catalytic efficient and stereoselectivity in direct Mannich reaction and green synthesis of (E)-a, β-unsaturated ketones. Based on our green catalytic system, we developed a reaction-induced self-separation catalytic system, which showed facile separation of the catalyst and product. After that, the relationship between structure and catalytic activity as well as diastereoselectivity was uncovered. In summary, by adopting the sulfur atom as linking atom, the catalytic efficient and stereoselective of the organobismuth complex was significantly improved and Lewis acidic/basic bifunctional catalysts were obtained.
4) By adopting nitrogen-bridged ligands (4a-4c) and changing the bismuth metal to antimony, air-stable5,6,7,12-tetrahydrodibenz[c,f)[1,5]azaantimocine framework were constructed, a serial of organoantimony chlorides (RN(C6H4CH2)2SbCl (R=tBu (11a), c-CeH11(11b), Ph (11e))) were successfully synthesized. By modification of counter anions, strong Lewis acidic organoantimony Lewis acid (RN(C6H4CH2)2BiX, R=c-CeH11, X=OSO2CF3(12a); R=Ph, BF4(12b), F (12c), Br (12d), I (12e)) were obtained. In one-pot three component Mannich reaction and ring-opening reaction of epoxide with amine, these complexes showed high catalytic activity and stereoselectivity, illustrating that by weakening of N-Sb atom bond strength, the long pair electrons of nitrogen atom can be also acted as Lewis basic site, implies that these organoantimony complexes may be acted as the self unquenched Lewis pairs. While the binuclear organoantimony complexes bridged by sulfur or oxygen atoms ([RN(C6H4CH2)2Sb]2O (R=tBu (14a), c-C6H11(14b), Ph (14c))) showed bimetallic cooperative catalytic activity in cyclic carbonate synthesis from expoxide and CO2compared with c-C6H11N(C6H4CH2)SbOMe (13a) and11a-11c.
本文针对有机金属路易斯酸存在的不足以及茂金属配合物和有机铋、锑配合物的特点,提出构建稳定的碳-金属键的同时,引入强拉电子能力的阴离子,设计合成了30余种耐水抗氧型有机金属路易斯酸催化剂,并采用NMR、X射线单晶衍射、TG-DSC等多种表征技术对有机金属路易斯酸配合物的组成、结构和物化性质进行了分析表征,还探讨了其在碳-杂键和碳-碳键形成反应等有机化工中具有重要作用有机反应中的催化应用,主要研究结果和结论如下：
1)采用具有稳定C-M键的茂金属氯化物Cp2MCl2(M=Zr (1a)、Hf(1b)、Ti(1c)),通过引入强拉电子能力的全氟烷基或芳基磺酸基团,构建了耐水抗氧型路易斯酸双核茂锆、茂铪路易斯酸配合物[(CpZr(OH2)3)2(μ2-OH)2][C6F5SO3]4·6H2(2a·6H2O)、[(CpHf(OH2)3)2(μ2-OH)2][OSO2C8F17]4·4H2O·2THF (2b·4H2O·2THF)]和单核茂锆、茂钛全氟烷基磺酸配合物Cp2M(OSO2C8F17)2·nH2O·THF (M=Zr (3a·3H2O·THF), Ti3b·(2H2O·THF))、 Cp2M(OSO2C4F9)2·nH2O (M=Zr (3c·2H2O), Ti (3d·2H2O))。实验表明,这6种配合物均为耐水抗氧的离子型茂金属配合物,金属与环戊二烯基形成稳定的碳-金属键,阴离子与金属的配位水分子形成氢键团簇在阳离子金属中心周围,从而产生耐水抗氧性能。这些配合物易溶于极性溶剂且具有与Sc(OTf)3相当的强酸性,能够催化如碳-碳键形成等有机合成反应。基于这些茂金属全氟磺酸配合物,开发了一种醇、酚、硫醇和胺的通用酰化方法,并可应用于生物柴油的合成。基于Cp2Zr(OSO2C8F17)2催化糖基化反应开发了葡萄糖骨架的生物活性分子合成法。基于Cp2Ti(OSO2C8F17)2/Zn粉催化体系,开发了硫(硒)代酯、α-硫(硒)代羰基化合物以及单硫(硒)醚化合物的简易绿色合成法。另外,还发现这些配合物为烯丙基化反应,Mukaiyama-aldol反应,Friedel-Crafts酰化反应,Mannich反应和酮自缩合芳构化反应等碳-碳键形成反应的高效催化剂。综上所述,本文成功合成了具有强酸性的耐水抗氧型茂金属全氟磺酸配合物,并可作为一种高效广谱的C-C键和C-Z(O, N, S, Se)键等成键反应的路易斯酸催化剂,在有机合成中具有广阔潜在应用前景。
2)合成了具有氮原子桥连的pincer配体4a-4c,构建了具有稳定的C-Bi键的氮原子桥连有机铋氯化物RN(C6H4CH2)2BiCl (R=tBu (5a), c-C6H11(5b), Ph (5c)),通过用强拉电子能力的阴离子置换其中的氯原子,构建了耐水抗氧型有机铋配合物路易斯酸催化剂c-C6H11N(C6H4CH2)2BiX (X=BF4(6a), OSO2CgF17(6b)),这些催化剂在烯丙基化反应和Mannich反应中表现出与过渡金属路易斯酸相当的优异催化性能。通过氧原子和硫原子桥连合成了双核的有机铋配合物[RN(C6H4CH2)2Bi]2X (X=O, R=tBu (8a), c-C6H11(8b), Ph (8c); X=S, R=tBu (9a), c-C6H11(9b), Ph (9c))。与单核的tBuN(C6H4CH2)2BiOMe (7a)和5a-5c相比,这类配合物在二氧化碳和环氧化物合成环状碳酸酯的催化反应中表现出明显的双金属协同催化效应。
3)合成了具有路易斯碱位的硫桥pincer配体4d,构建具有稳定的C-Bi键的硫桥有机铋氯化物S(C6H4CH2)2BiCl (5d),通过用强拉电子能力的阴离子置换其中的氯原子,构建了耐水抗氧型路易斯酸碱双功能催化剂S(C6H4CH2)2Bi(OH2)X (X=ClO4(10a), BF4(10b), OSO2C4F9(10c), OSO2CgF17(10d))。这类催化剂在直接非对映异构选择性Mannich反应和(E)-α,β-不饱和酮的绿色立体专一性合成反应中表现出很高的催化活性和立体选择性。基于这一绿色催化体系,开发了反应控制的自分离催化体系,实现了催化剂和产物的自动分离。另外还阐述了配合物结构与催化活性之间的构-效关系。总之,通过引入硫原子代替氮原子,极大的改善了有机铋配合物的催化活性和立体选择性,构建了对空气稳定的有机铋路易斯酸、碱双功能催化剂。
4)采用相同的配体4a-4c构建5,6,7,12-四氢二苯并[c,f][1,5]氮锑辛烯骨架,构建了对空气稳定的有机锑氯化物RN(C6H4CH2)2SbCl (R=tBu (11a), c-C6H11(11b), Ph(11c)),通过调变其中的对应阴离子,获得了具有较强路易斯酸性的有机锑配合物(RN(C6H4CH2)2BiX, R=c-C6H11, X=OSO2CF3(12a); R=Ph, BF4(12b), F (12c), Br (12d), I(12e)),并且发现有机锑配合物路易斯酸12a和12c在Mannich反应和环氧化物的胺解反应中表现出了很好的催化活性和立体选择性,这说明通过调变N-Sb键的键强可以调变配位原子的配位能力,使得参与配位的氮原子上的孤对电子可以同时作为路易斯碱中心,可被认为是不自我淬灭的路易斯酸碱对。另外,通过氧原子桥连合成了双核有机锑配合物[(?)N(C6H4CH2)2Sb]2O (R=tBu (14a), c-C6H11(14b),Ph(14c))。与单核的(13a)和11a-11c相比,这类配合物在二氧化碳和环氧化物合成环状碳酸酯的催化反应中表现出明显的双金属协同催化效应。
Organometallic Lewis acid plays an important role in modern organic synthesis. During the past two decades the uninterrupted expansion of this field has continued. New Lewis acid research is targeting more versatile, more selective, more reactive, more stable, cheaper, and greener catalysts. Up to now, the development of organometallic Lewis acid has suffered from several shortcomings:(1) Partial organometallic Lewis acids are air-or moisture-sensitive, lower Lewis acidic, poor catalytic active and selective catalyst;(2) It is hard to achieve both properties of strong Lewis acidity and high stability in a same Lewis catalytic system;(3) The Lewis acid catalyst is high toxic or catalytic system is not environmental-friendly;(4) The metal adopted in some of organometallic complexes are too expansive to use in wide application;(5) most of organometallic Lewis acids are not versatile for many kinds of reactions. With the emphasized on the "green" and "sustainable" chemistry, how to design and synthesis of high catalytic efficient, cheaper, stable and versatile green organometallic Lewis acid is the key issue in modern organometallic Lewis acid catalysis chemistry.
Based on the shortcomings of the organometallic Lewis acid chemistry and metallocence and organobismuth and organoantimony special features, by construction of stable C-M bond and incorporation of larger electronic-withdrawing group, a serial of air-stable, water-tolerant organometallic Lewis acid catalysts were synthesized and characterized by NMR, X-ray single crystal diffraction and TG-DSC technologies, etc to demonstrate their composition, structure and physical or chemical properties. Moreover, their applications in construction of carbon-heteroatom and carbon-carbon bond formation were also investigated. Some innovative results and conclusions were obtained as follows:
1) By incorporation of larger electronic-withdrawing long chain perfluoroalkyl group ion to place the chloride in Cp2MCl2(M=Zr (1a)、Hf (1b)、Ti (1c)), air-stable and water-tolerant metallocene complex Lewis acid catalysts ([(CpZr(OH2)3)2(μ2-OH)2][C6F5SO3]4·6H2O (2a·6H2O),[(CpHf(OH2)3)2(μ2-OH)2][OSO2C8F17]4·4H2O·2THF (2b·4H2O·2THF)},Cp2M(OSO2C8F17)2·nH2O·THF (M=Zr (3a·3H2O·THF), Ti3b·(2H2O·THF)) and Cp2M(OSO2C4F9)2·nH2O (M=Zr (3c·2H2O), Ti (3d·2H2O))) were synthesized. These complexes can be stable in the open air for a month or a year and remain as dry crystal or white powders. The anions are packed around the complex cation in such a way that their oxygen atoms point towards the H2O ligands.
The perfluoroalkyl group sides of the anion, on the other hand, are clustered together to form the hydrophobic domains. These complexes showed heat resistant and high solubility in polar organic solvent. Furthermore, they also showed high Lewis acidity in the same level as that of Sc(OTf)3, which can be used to promote carbon-carbon bond formation. Based on these complexes, we developed a versatile acylation method for alcohol, phenol, thiol and amine, which can be applied in biodiesel synthesis. Cp2Zr(OSO2C8F17)2can be also used in glycosylation to prepare bioactive molecules. Based on the Cp2Ti(OSO2CgF17)2/Zn dust catalytic system, we developed a simple, efficient and green synthetic method to prepare thio(seleno)ester, a-thio(seleno)carbonyl compounds and thio(seleno)ether. These metallocene Lewis acid catalysts also showed high catalytic efficient in allylation, Mukaiyama-aldol reaction, Friedel-Crafts acylation, Mannich reaction, and cyclotrimerization of ketones. In a word, the metallocene complexes can be used as versatile organometallic Lewis acid catalyst in various carbon-carbon bond and carbon-heteroatom formation reactions. On account of its stability, storability, and versatile ability, these complexes should find broad catalytic applications in organic synthesis.
2) By design and synthesis of nitrogen-bridged ligands (4a-4c), the organobismuth chlorides RN(C6H4CH2)2BiCl (R=tBu (5a), c-C6H11(5b), Ph (5c)) with stable C-Bi bonds were synthesized. By incorporation of larger electronic-withdrawing counter anion to replace the chloride, air-stable and water-tolerant organobismuth complex Lewis acids c-C6H11N(C6H4CH2)2BiX (X=BF4(6a), OSO2C8F17(6b)) were synthesized. They showed high air-stability and Lewis acidity as well as heat resistant and can be applied as catalyst in Mannich reaction and allylation reaction. While the binuclear organobismuth complexes bridged by sulfur or oxygen atoms ([RN(C6H4CH2)2Bi]2X (X=O, R=tBu (8a), c-C6H11(8b), Ph(8c); X=S, R=tBu (9a), c-C6H11(9b), Ph (9c))) showed bimetallic cooperative catalytic activity in cyclic carbonate synthesis from epoxide and CO2compared with tBuN(C6H4CH2)2BiOMe (7a) and5a-5c.
3) By adopting sulfur bridged pincer ligand (4d) with suitable Lewis basic site, an organobismuth chloride (5d) bearing stable C-Bi bonds was synthesized. By incorporation of larger electronic-withdrawing counter anion to place the chloride, air-stable and water-tolerant sulfur bridged organobismuth complex Lewis acids S(C6H4CH2)2Bi(OH2)X (X=ClO4(10a), BF4(10b), OSO2C4F9(10c), OSO2C8F17(10d)) were synthesized. With the exposed bismuth center acting as Lewis acid site and the uncoordinated lone pair electrons of sulfur as Lewis base site, the cationic organobismuth complexes work as bifunctional Lewis acid/base catalysts. These complexes showed high catalytic efficient and stereoselectivity in direct Mannich reaction and green synthesis of (E)-a, β-unsaturated ketones. Based on our green catalytic system, we developed a reaction-induced self-separation catalytic system, which showed facile separation of the catalyst and product. After that, the relationship between structure and catalytic activity as well as diastereoselectivity was uncovered. In summary, by adopting the sulfur atom as linking atom, the catalytic efficient and stereoselective of the organobismuth complex was significantly improved and Lewis acidic/basic bifunctional catalysts were obtained.
4) By adopting nitrogen-bridged ligands (4a-4c) and changing the bismuth metal to antimony, air-stable5,6,7,12-tetrahydrodibenz[c,f)[1,5]azaantimocine framework were constructed, a serial of organoantimony chlorides (RN(C6H4CH2)2SbCl (R=tBu (11a), c-CeH11(11b), Ph (11e))) were successfully synthesized. By modification of counter anions, strong Lewis acidic organoantimony Lewis acid (RN(C6H4CH2)2BiX, R=c-CeH11, X=OSO2CF3(12a); R=Ph, BF4(12b), F (12c), Br (12d), I (12e)) were obtained. In one-pot three component Mannich reaction and ring-opening reaction of epoxide with amine, these complexes showed high catalytic activity and stereoselectivity, illustrating that by weakening of N-Sb atom bond strength, the long pair electrons of nitrogen atom can be also acted as Lewis basic site, implies that these organoantimony complexes may be acted as the self unquenched Lewis pairs. While the binuclear organoantimony complexes bridged by sulfur or oxygen atoms ([RN(C6H4CH2)2Sb]2O (R=tBu (14a), c-C6H11(14b), Ph (14c))) showed bimetallic cooperative catalytic activity in cyclic carbonate synthesis from expoxide and CO2compared with c-C6H11N(C6H4CH2)SbOMe (13a) and11a-11c.
引文
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