二茂铁基咪唑啉环钯化合物催化的Suzuki偶联反应的研究
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摘要
本论文合成了二茂铁基咪唑啉及其环钯化合物并对其在催化Suzuki偶联反应中的应用进行了研究。论文的主要内容包括以下几个方面:
第一章:对近年来钯催化的Suzuki偶联反应的研究进展进行了的综述,主要从催化剂及其在Suzuki反应中的应用进行了的介绍和讨论。
第二章:利用手性氨基酸作为手性源方面的优势,结合二茂铁独特的电子效应和空间立体效应,合成了以L-苯丙氨酸和缬氨酸为手性源的新型二茂铁基咪唑啉环钯化合物5(a-h)。同时,获得化合物6a的单晶,对其进行了X-ray单晶衍射测定。
第三章:以二茂铁咪唑啉环钯化合物5(a-h)为催化剂研究了4-溴苯甲醚与苯硼酸的Suzuki偶联反应,并探讨了影响Suzuki偶联反应的各个因素,得到了最优化的反应条件:甲苯为溶剂,K_3PO_4·3H_2O为碱,反应温度为110℃。在最佳条件下,研究了卤代芳烃和苯硼酸的偶联反应,结果表明,该类环钯化合物均能够很好的催化Suzuki偶联反应,并且在空气中稳定,对环境无污染。
第四章:以二茂铁咪唑啉环钯化合物5a为催化剂,在室温条件下研究了影响Suzuki偶联反应的各个因素,得到了最优化的反应条件:甲醇和水的混合溶液为溶剂,KOH为碱,n-Bu_4NBr为表面活性剂。在最优化的条件下,研究了卤代芳烃与苯硼酸的偶联反应。从环保和经济的角度出发,室温下催化的Suzuki偶联反应更具有实用价值。
In this thesis, novel ferocenylimidazolines and their cyclopalladated complexes were easily synthesized and successfully used in palladium-catalyzed Suzuki cross-coupling.
Chapter 1: Progress in the palladium-catalyzed Suzuki cross-coupling reaction were summarized. The development of catalysts in the Suzuki cross-coupling reaction and the applications of the Suzuki cross-coupling reaction in the organic synthesis were discussed.
Chapter 2: The new ferrocenylimidazoline cyclopalladated complexes 5(a-h) derived from L-phenylalanine and valine were synthesized. At the same time, we also gained depolymerization of single crystal monomer compound 6a, which was characterized by X-ray single crystal diffraction.
Chapter 3: The use of these ferrocenylimidazoline cyclopalladated complexes 5(a-h) as catalysts in Suzuki reactions was examined under the heating condition. They were found to be very efficient in the Suzuki reaction of 1-bromo-4-methoxybenzene with phenylboronic acid. The effection of different conditions on the Suzuki cross-coupling reaction were studied, Toluene was used as solvent, K_3PO_4·3H_2O was added as base, the temperature was 110℃, and the optimal reaction conditions were gained. Under the optimal reaction conditions, the Suzuki reaction of aryl halides with arylboronic acids was performed which was found that the cyclopalladated complexes could catalyze the Suzuki reaction efficiently. The catalysts was found stable and did not decompose in the air and without environment pollution.
Chapter 4: The different reaction conditions of the Suzuki cross-coupling reaction catalyzed with ferrocenylimidazoline cyclopalladated complexes 5(a-h) at the room temperature was explored. The effection of different conditions on the Suzuki cross-coupling reaction were studied, methanol and water were used as solvent, KOH was added as base, n-Bu_4NBr was used as the additive, and the Suzuki reaction between aryl halides and arylboronic acids under the optimal condition. For a better result from economy and circunstance protection, the Suzuki reaction catalysted in the room temperature is more useful in practice.
第一章:对近年来钯催化的Suzuki偶联反应的研究进展进行了的综述,主要从催化剂及其在Suzuki反应中的应用进行了的介绍和讨论。
第二章:利用手性氨基酸作为手性源方面的优势,结合二茂铁独特的电子效应和空间立体效应,合成了以L-苯丙氨酸和缬氨酸为手性源的新型二茂铁基咪唑啉环钯化合物5(a-h)。同时,获得化合物6a的单晶,对其进行了X-ray单晶衍射测定。
第三章:以二茂铁咪唑啉环钯化合物5(a-h)为催化剂研究了4-溴苯甲醚与苯硼酸的Suzuki偶联反应,并探讨了影响Suzuki偶联反应的各个因素,得到了最优化的反应条件:甲苯为溶剂,K_3PO_4·3H_2O为碱,反应温度为110℃。在最佳条件下,研究了卤代芳烃和苯硼酸的偶联反应,结果表明,该类环钯化合物均能够很好的催化Suzuki偶联反应,并且在空气中稳定,对环境无污染。
第四章:以二茂铁咪唑啉环钯化合物5a为催化剂,在室温条件下研究了影响Suzuki偶联反应的各个因素,得到了最优化的反应条件:甲醇和水的混合溶液为溶剂,KOH为碱,n-Bu_4NBr为表面活性剂。在最优化的条件下,研究了卤代芳烃与苯硼酸的偶联反应。从环保和经济的角度出发,室温下催化的Suzuki偶联反应更具有实用价值。
In this thesis, novel ferocenylimidazolines and their cyclopalladated complexes were easily synthesized and successfully used in palladium-catalyzed Suzuki cross-coupling.
Chapter 1: Progress in the palladium-catalyzed Suzuki cross-coupling reaction were summarized. The development of catalysts in the Suzuki cross-coupling reaction and the applications of the Suzuki cross-coupling reaction in the organic synthesis were discussed.
Chapter 2: The new ferrocenylimidazoline cyclopalladated complexes 5(a-h) derived from L-phenylalanine and valine were synthesized. At the same time, we also gained depolymerization of single crystal monomer compound 6a, which was characterized by X-ray single crystal diffraction.
Chapter 3: The use of these ferrocenylimidazoline cyclopalladated complexes 5(a-h) as catalysts in Suzuki reactions was examined under the heating condition. They were found to be very efficient in the Suzuki reaction of 1-bromo-4-methoxybenzene with phenylboronic acid. The effection of different conditions on the Suzuki cross-coupling reaction were studied, Toluene was used as solvent, K_3PO_4·3H_2O was added as base, the temperature was 110℃, and the optimal reaction conditions were gained. Under the optimal reaction conditions, the Suzuki reaction of aryl halides with arylboronic acids was performed which was found that the cyclopalladated complexes could catalyze the Suzuki reaction efficiently. The catalysts was found stable and did not decompose in the air and without environment pollution.
Chapter 4: The different reaction conditions of the Suzuki cross-coupling reaction catalyzed with ferrocenylimidazoline cyclopalladated complexes 5(a-h) at the room temperature was explored. The effection of different conditions on the Suzuki cross-coupling reaction were studied, methanol and water were used as solvent, KOH was added as base, n-Bu_4NBr was used as the additive, and the Suzuki reaction between aryl halides and arylboronic acids under the optimal condition. For a better result from economy and circunstance protection, the Suzuki reaction catalysted in the room temperature is more useful in practice.
引文
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[103] Littke A F, Fu G C. A Convenient and General Method for Pd-Catalyzed Suzuki Cross- Couplings of Aryl Chlorides and Arylboronic Acids. Angew. Chem. Int. Ed., 1998, 37: 3387-3388.
[104] Littke A F, Dai C, Gu G C. Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions. J Am. Chem. Soc., 2000, 122: 4020-4028.
[105] Old D W, Wolfe J P, Buchwald S L. A Highly Active Catalyzed Amination Catalyst for Palladium-Suzuki Couplings and Cross-Coupling Reactions: Room-Temperature of Unacti- vated Aryl Chlorides. J. Am. Chem. Soc., 1998, 120: 9722-9723.
[106] Wolfe J P, Buchwald S L. A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides. Angew Chem. Int. Ed., 1999, 38: 2413-2416.
[107] Wolfe J P, Singer R A, Yang B H et al. Highly Active Palladium Catalysts for Suzuki Coupling Reactions. J. Am. Chem. Soc., 1999, 121: 9550-9561.
[108] Walker S D, Barder T E, Martinelli J R et al. A Rationally Designed Universal Catalyst for Suzuki-Miyaura Coupling Processes. Angew Chem. Int. Ed., 2004, 43: 1871-1876.
[109] Barder T E, Walker S D, Martinelli J R et al. Catalysts for Suzuki-Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure. J. Am. Chem. Soc., 2005, 127: 4685-4696.
[110] Altenhoff G, Goddard R, Lehmann C W et al. Sterically Demanding, Bioxazoline- Derived N-Heterocyclic Carbene Ligands with Restricted Flexibility for Catalysis. J. Am. Chem. Soc., 2004, 126: 15195-15201.
[111] Navarro O, Marion N, Oonishi Y et al. Suzuki-Miyaura,α-Ketone Arylation and Dehalogenation Reactions Catalyzed by a Versatile N-Heterocyclic Carbene- Palladacycle Complex. J. Org. Chem., 2006, 71: 685-692.
[112] Singh R, Viciu M S, Kramareva N K et al. Simple (Imidazol-2- ylid- ene)-Pd-Acetate Complexes as Effective Precatalysts for Sterically Hindered Suzuki-Miyaura Couplings. Org. Lett., 2005, 7: 1829-1832.
[113] Marion N, Navarro O, Jianguo M et al. Modified (NHC)Pd(allyl)Cl (NHC=N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions. J. Am. Chem. Soc., 2006, 128: 4101-4111.