二茂铁基咪唑啉环钯化合物的合成及其在催化反应中的应用研究
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摘要
本论文对二茂铁基咪唑啉及其环钯化合物的合成及其在催化反应中的应用进行了以下研究：
一、二茂铁基咪唑啉化合物的合成与结构表征
以二茂铁亚胺酸甲酯和相应二胺：1，2—二苯基乙二胺、N—正戊基乙二胺、N—正辛基乙二胺、N—正十四基乙二胺等为原料，合成了系列新型二茂铁基咪唑啉化合物(Scheme 1)，并对这些化合物进行了元素分析、核磁共振、红外光谱、熔点等表征。探索了带有不同取代基二茂铁基咪唑啉的合成方法。
二、二茂铁基咪唑啉环钯化合物的合成与表征
首次合成了系列新型二茂铁基咪唑啉环钯化合物二聚体6和单体7(Scheme2)，通过元素分析、红外光谱、核磁共振等对其结构进行了表征，其中化合物7a、7d和7g经X—射线单晶衍射确定其结构。环钯二聚体的溶解度受1位N上的取代基影响较大，当1位N上连有斥电基团时，如长链烷基，环钯二聚体的溶解度大于吸电基团的环钯二聚体的溶解度，如乙酰基。
三、二茂铁基咪唑啉环钯化合物在Aza-Claisen反应中的应用
探索了以二茂铁基咪唑啉环钯化合物6为催化剂，在无辅助催化剂Ag和TI盐的情况下催化Aza-Claisen反应。研究了催化剂的活性和Aza-Claisen重排反应的影响因素，发现配体中1位N上的取代基影响催化剂的溶解度，而溶解度大小决定着催化剂的催化活性；同时也发现了底物中N—苯环上取代基的电子效应是Aza-Claisen重排反应的重要影响因素之一，给电子基团有利于反应进行，而吸电子取代基则不利于反应进行。
四、二茂铁基咪唑啉环钯化合物在Suzuki反应中的应用
研究了二茂铁基咪唑啉环钯化合物6在溴代芳烃和芳基硼酸的Suzuki偶联反应，考察了碱、催化剂、底物对反应的影响，优化了催化反应条件，发现在甲苯110℃时以K_3PO_4·7H_2O为碱，无惰性气体保护，以环钯化合物6为催化剂，以0.1mol％的用量能有效地催化溴代芳烃和芳基硼酸的偶联反应，其中对较不活泼的2—溴噻吩与苯基硼酸的偶联反应，催化剂6b给出了96％的偶联产物。
五、二茂铁基咪唑啉环钯化合物6b在室温下催化Suzuki反应中的应用
研究了环钯化合物6b催化溴代芳烃和芳基硼酸在室温下的偶联反应，考察了碱、溶剂、TBAB、底物对反应的影响。结果表明室温下，以K_2CO_3为碱，甲醇／水(2：1)为溶剂，TBAB作为添加剂，催化剂用量0.5mol％，可以有效地催化溴代芳烃和芳基硼酸的偶联反应。
In this thesis, the properties and synthesis of ferrocenylimidazolines and their cyclopalladated complexes, the palladacycle-catalyzed Aza-Claisen rearrangement reaction, Suzuki reaction have been studied as follows:
1) Synthesis and characterization of novel ferrocenylimidazolines
A series of novel ferrocenylimidazolines (5) were synthesized by the condensation of ferrocenylimidic acid methyl ester hydrochloride (3) with corresponding diamines (4) (Scheme 1). The products were characterized by elemental analysis, IR and NMR spectra. The synthetic methods of ferrocenylimidazolines with different substituents in the imidazoline ring have been developed.
2) Synthesis and characterization of cyclopalladated ferrocenylimidazolines
The reaction of the compounds 5 with Li_2PdCl_4 in the presence of sodium acetate gave seven novel chloride-bridged palladacycle dimers 6, which was treated with 2 equivalent of triphenylphosphine (PPh_3) in methanol at room temperature to produce the corresponding triphenylphosphine (PPh_3) adduct 7 (Scheme 2). These new cyclopalladated complexes were characterized by elemental analysis, IR, NMR spectra. The compounds 7a, 7d and 7g were further confirmed by single crystal X-ray diffraction.
3) The appfication of ferrocenylimidazoline palladacycles in Aza-Clasien rearrangement reactions
Chloride-bridged palladacycle dimers 6 have been evaluated as highly efficient catalysts for the aza-Claisen rearrangement reaction of allylic imidates without activation with silver and thallium salts. The correlation between the substituents on the imidazoline ring and catalytic activity of palladacycles was established. Additionally, the effect of nature of substrates should also be taken into account.
4) The application of new ferrocenylimidazoline palladacycles 6 in Suzuki cross coupling reactions
Chloride-bridged palladacycle dimers 6, which are thermally stable and insensitive to air and moisture, have been evaluated as effective phosphine-free catalysts for the Suzuki reaction of aryl bromides with arylboronic acid. The catalyst 6b presents the highest efficiency in the coupling processes for less reactive 2-bromothiophene. K_3PO_4·7H_2O was found to be the best base and a small amount of water was essential for this catalytic system.
5) The application of ferrocenylimidazoline palladacycle 6b in catalyzed Suzuki cross coupling reaction at room temperature
The novel ferrocenylimidazoline palladacycle 6b was successfully used in Suzuki cross coupling reaction of aryl bromide with with arylboronic acid at room temperature. The coupled products were obtained in excellent yields for the less active aryl bromides with bromides with arylboronic acids with 0.5mol% loading of 6b in the presence of 2 equivalent of K_2CO_3 as base and 1 equivalent TBAB as additive at room temperature.
Ar-Br+Ar'B(OH)_2(?)Ar'-Ar
一、二茂铁基咪唑啉化合物的合成与结构表征
以二茂铁亚胺酸甲酯和相应二胺：1，2—二苯基乙二胺、N—正戊基乙二胺、N—正辛基乙二胺、N—正十四基乙二胺等为原料，合成了系列新型二茂铁基咪唑啉化合物(Scheme 1)，并对这些化合物进行了元素分析、核磁共振、红外光谱、熔点等表征。探索了带有不同取代基二茂铁基咪唑啉的合成方法。
二、二茂铁基咪唑啉环钯化合物的合成与表征
首次合成了系列新型二茂铁基咪唑啉环钯化合物二聚体6和单体7(Scheme2)，通过元素分析、红外光谱、核磁共振等对其结构进行了表征，其中化合物7a、7d和7g经X—射线单晶衍射确定其结构。环钯二聚体的溶解度受1位N上的取代基影响较大，当1位N上连有斥电基团时，如长链烷基，环钯二聚体的溶解度大于吸电基团的环钯二聚体的溶解度，如乙酰基。
三、二茂铁基咪唑啉环钯化合物在Aza-Claisen反应中的应用
探索了以二茂铁基咪唑啉环钯化合物6为催化剂，在无辅助催化剂Ag和TI盐的情况下催化Aza-Claisen反应。研究了催化剂的活性和Aza-Claisen重排反应的影响因素，发现配体中1位N上的取代基影响催化剂的溶解度，而溶解度大小决定着催化剂的催化活性；同时也发现了底物中N—苯环上取代基的电子效应是Aza-Claisen重排反应的重要影响因素之一，给电子基团有利于反应进行，而吸电子取代基则不利于反应进行。
四、二茂铁基咪唑啉环钯化合物在Suzuki反应中的应用
研究了二茂铁基咪唑啉环钯化合物6在溴代芳烃和芳基硼酸的Suzuki偶联反应，考察了碱、催化剂、底物对反应的影响，优化了催化反应条件，发现在甲苯110℃时以K_3PO_4·7H_2O为碱，无惰性气体保护，以环钯化合物6为催化剂，以0.1mol％的用量能有效地催化溴代芳烃和芳基硼酸的偶联反应，其中对较不活泼的2—溴噻吩与苯基硼酸的偶联反应，催化剂6b给出了96％的偶联产物。
五、二茂铁基咪唑啉环钯化合物6b在室温下催化Suzuki反应中的应用
研究了环钯化合物6b催化溴代芳烃和芳基硼酸在室温下的偶联反应，考察了碱、溶剂、TBAB、底物对反应的影响。结果表明室温下，以K_2CO_3为碱，甲醇／水(2：1)为溶剂，TBAB作为添加剂，催化剂用量0.5mol％，可以有效地催化溴代芳烃和芳基硼酸的偶联反应。
In this thesis, the properties and synthesis of ferrocenylimidazolines and their cyclopalladated complexes, the palladacycle-catalyzed Aza-Claisen rearrangement reaction, Suzuki reaction have been studied as follows:
1) Synthesis and characterization of novel ferrocenylimidazolines
A series of novel ferrocenylimidazolines (5) were synthesized by the condensation of ferrocenylimidic acid methyl ester hydrochloride (3) with corresponding diamines (4) (Scheme 1). The products were characterized by elemental analysis, IR and NMR spectra. The synthetic methods of ferrocenylimidazolines with different substituents in the imidazoline ring have been developed.
2) Synthesis and characterization of cyclopalladated ferrocenylimidazolines
The reaction of the compounds 5 with Li_2PdCl_4 in the presence of sodium acetate gave seven novel chloride-bridged palladacycle dimers 6, which was treated with 2 equivalent of triphenylphosphine (PPh_3) in methanol at room temperature to produce the corresponding triphenylphosphine (PPh_3) adduct 7 (Scheme 2). These new cyclopalladated complexes were characterized by elemental analysis, IR, NMR spectra. The compounds 7a, 7d and 7g were further confirmed by single crystal X-ray diffraction.
3) The appfication of ferrocenylimidazoline palladacycles in Aza-Clasien rearrangement reactions
Chloride-bridged palladacycle dimers 6 have been evaluated as highly efficient catalysts for the aza-Claisen rearrangement reaction of allylic imidates without activation with silver and thallium salts. The correlation between the substituents on the imidazoline ring and catalytic activity of palladacycles was established. Additionally, the effect of nature of substrates should also be taken into account.
4) The application of new ferrocenylimidazoline palladacycles 6 in Suzuki cross coupling reactions
Chloride-bridged palladacycle dimers 6, which are thermally stable and insensitive to air and moisture, have been evaluated as effective phosphine-free catalysts for the Suzuki reaction of aryl bromides with arylboronic acid. The catalyst 6b presents the highest efficiency in the coupling processes for less reactive 2-bromothiophene. K_3PO_4·7H_2O was found to be the best base and a small amount of water was essential for this catalytic system.
5) The application of ferrocenylimidazoline palladacycle 6b in catalyzed Suzuki cross coupling reaction at room temperature
The novel ferrocenylimidazoline palladacycle 6b was successfully used in Suzuki cross coupling reaction of aryl bromide with with arylboronic acid at room temperature. The coupled products were obtained in excellent yields for the less active aryl bromides with bromides with arylboronic acids with 0.5mol% loading of 6b in the presence of 2 equivalent of K_2CO_3 as base and 1 equivalent TBAB as additive at room temperature.
Ar-Br+Ar'B(OH)_2(?)Ar'-Ar
引文
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