原位生成的水溶性Salen-Pd配合物催化微波促进水中的C-C偶联反应
|
摘要
将一种水溶性Salen, N,N’-双[(5-磺酸基-2-羟基)苄基]缩N,N’-二甲基-1,2-乙二胺(L)与醋酸钯原位生成水溶性Salen-Pd配合物,该水溶性钯配合物应用于催化微波加热的水中的Heck和Sonogashira碳-碳偶联反应.在优化反应条件之后,对溴苯衍生物与乙烯衍生物的Heck偶联反应以及溴苯衍生物与苯乙炔及其衍生物之间的Sonogashira偶联反应进行了考察.发现,在优化的反应条件下,无论是Heck反应,还是Sonogashira偶联反应,都能得到很好的收率.在有机物分离之后,水相继续循环使用4次,在水相的前3次循环使用时,都获得了不错的收率.
The water-soluble Salen-Pd complex was made in situ with mixture of N,N'-bis [(5-sulfonato-2-hydroxy)benzyl]-N,N'-dimethyl-ethane-1,2-diaminen and palladium acetate in water. This complex was used as catalyst for microwave-promoted Heck and Sonogashira coupling reaction. Under the optimal reaction conditions, the Heck reaction of bromobenzene and its derivatives with ethylene derivatives, and the Sonogashira coupling reaction of bromobenzene's derivatives with phenylacetylene and its derivatives, were investigated. It was found that under the optimal reaction conditions, the yields of both Heck reactions and Sonogashira coupling reactions were good to excellent. Under the same reaction condition, the aqueous phase was reused 4 times for Heck reactions and Sonogashira coupling reactions, And the results indicated that the aqueous phase still had good catalytic activity in the first three recycles.
The water-soluble Salen-Pd complex was made in situ with mixture of N,N'-bis [(5-sulfonato-2-hydroxy)benzyl]-N,N'-dimethyl-ethane-1,2-diaminen and palladium acetate in water. This complex was used as catalyst for microwave-promoted Heck and Sonogashira coupling reaction. Under the optimal reaction conditions, the Heck reaction of bromobenzene and its derivatives with ethylene derivatives, and the Sonogashira coupling reaction of bromobenzene's derivatives with phenylacetylene and its derivatives, were investigated. It was found that under the optimal reaction conditions, the yields of both Heck reactions and Sonogashira coupling reactions were good to excellent. Under the same reaction condition, the aqueous phase was reused 4 times for Heck reactions and Sonogashira coupling reactions, And the results indicated that the aqueous phase still had good catalytic activity in the first three recycles.
引文
[1] Trilla M, Borja G, Pleixats R, et al. Recoverable palladium catalysts for Suzuki-Miyaura cross-coupling reactions based on organic-inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts [J]. Adv Synth Catal, 2008, 350(16): 2566-2574.
[2] a. Veerakumar P, Velayudham M, Lu K L, et al. Silica-supported PEI capped nanopalladium as potential catalyst in Suzuki, Heck and Sonogashira coupling reactions [J]. Appl Catal A, 2013, 455: 247-260.b. Cui Feng-juan(崔凤娟), Wang Huan-yu(王环宇), Deng Qing-fang(邓庆芳), et al. Cross-Coupling reaction of aryl halides with grignard reagents catalyzed by nickel complexes supported 2-pyrazolinyl-9-aryl-1, 10-phenanthrolines (2-吡唑啉-9-芳基邻菲咯啉镍配合物催化芳基卤化物和格氏试剂偶联反应的研究) [J]. J Mol Catal(China)(分子催化), 2018, 32(5): 397-404.
[3] Yan Mei(颜美), Feng Xiu-juan(冯秀娟). Advances in Suzuki coupling reactions catalyzed by supported palladium catalysts (负载钯催化的Suzuki偶联反应研究进展) [J]. Chin J Org Chem(有机化学), 2010, 30(5): 623-632.
[4] Danoun K, Essamlali Y, Amadine O, et al. Nanostructured pyrophosphate Na2PdP2O7-catalyzed Suzuki-Mi- yaura cross-coupling under microwave irradiation [J]. Appl Org Chem, 2018, 32(4): e4232.
[5] Shen X, Jones G O, Watson D A, et al. Enantioselective synthesis of axially chiral biaryls by the Pd-catalyzed Suzuki-Miyaura reaction: Substrate scope and quantum mechanical investigations [J]. J Am Chem Soc, 2010, 132(32): 11278-11287.
[6] Felpin F-X, Fouquet E, Zakli C. Improved Suzuki-Miyaura reactions of aryldiazonium salts with boronic acids by tuning palladium on charcoal catalyst properties [J]. Adv Synth Catal, 2009, 351(5): 649-655.
[7] Wu L, Li Z-W, Zhang F, et al. Air-stable and highly active dendritic phosphine oxide-stabilized palladium nano- particles: Preparation, characterization and applications in the carbon-carbon bond formation and hydrogenation reactions [J]. Adv Synth Catal, 2008, 350(6): 846-862.
[8] Manjunatha S G, Rangappa P, Sythana S, et al. A simple way of recycling of homogeneous catalyst in Suzuki reaction [J]. Green Chem Lett Rev, 2013, 6(1): 77-87.
[9] Liu Wen(刘文), Zheng Long-zhen(郑龙珍), Li Yi-di(李引弟). Synthesis of palladium-graphene oxide-Fe3O4 catalyst and its application in Heck reaction (Fe3O4-氧化石墨烯-钯催化剂的制备及其对Heck 反应催化研究) [J]. J Mol Catal (China) (分子催化), 2011, 25(6): 549-556.
[10] Shen Bin(沈彬), Li You (李游), Wang Zhi-fei(王志飞), et al. Catalytic activity of palladium supported on magnetic nanoparticles for Heck reaction (磁性纳米颗粒负载钯催化剂对Heck 反应的催化活性) [J]. Chin J Catal (催化学报), 2007, 28(6): 509-513.
[11] Huang Jin (黄锦), Wang Wei(汪伟). Palladium-tetraphosphine catalyzed Heck coupling reaction (钯和四齿磷配体催化剂应用于Heck反应研究) [J]. J Mol Catal (China) (分子催化), 2018, 32(4): 342-348.
[12] Zhou Y-B, Wang Y-Q,Ning L-C, et al. Conjugated microporous polymer as heterogeneous ligand for highly selective oxidative Heck reaction [J]. J Am Chem Soc, 2017, 139(10): 3966-3969.
[13] Li H J, Wang L. Triethanolamine as an efficient and reusable base, ligand and reaction medium for phosphane-free palladium-katalyzed Heck reactions [J]. Eur J Org Chem, 2006, 2006(22): 5099-5102.
[14] Yu J, Hong Z,Yang X, et al. Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: Synthesis of axitinib [J]. Beilstein J Org Chem 2018, 14(4): 786-795.
[15] Gazvoda M, Virant M, Pinter B, et al. Mechanism of copper-free Sonogashira reaction operates through palladium-palladium transmetallation [J]. Nat Commun, 2018, 9(11): 4814.
[16] Liang B, Dai M, Chen J, et al. Mechanism of copper-free Sonogashira reaction operates through palladium-palladium transmetallation [J]. J Org Chem, 2005, 70(1): 391-393.
[17] Corma A, Huárez R, Boronat M, et al. Gold catalyzes the Sonogashira coupling reaction without the requirement of palladium impurities [J]. Chem Commun, 2011, 47(5): 1446-1448.
[18] Cheng J, Sun Y, Wang F, et al. A copper- and amine-free Sonogashira reaction employing aminophosphines as ligands [J]. J Org Chem, 2004, 69(16): 5428-5432.
[19] Li Hong-lin(李红玲), Zhang Xia(张霞), Lin Hong-tao(蔺红桃), et al. Phosphine free, copper free palladium catalyzed Sonogashira cross-coupling reactions in ionic liquids (离子液体中无磷、无铜、钯催化的Sonogashira交联反应研究) [J]. J Mol Catal (China) (分子催化), 2009, 23(5): 412-417.
[20] Gholinejad M, Bahrami M, Najera C, et al. Magnesium oxide supported bimetallic Pd/Cu nanoparticles as an efficient catalyst for Sonogashira reaction [J]. J Catal, 2018, 363: 81-91.
[21] Beletskaya I P, Cheprakov A V. The Heck reaction as a sharpening stone of palladium catalysis [J]. Chem Rev, 2000, 100(8): 3009-3066.
[22] Dounay A B, Overman L E. The asymmetric intramolecular Heck reaction in natural product total synthesis [J]. Chem Rev, 2003, 103(8): 2954-2963.
[23] KongSheng-nan(孔胜男), Malik A U, Qian Xue-feng(钱雪峰), et al. C-C coupling reactions in water catalyzed by palladium(II) supported on microporous organic polymer (水相中微孔有机聚合物负载钯催化的碳-碳偶联反应) [J]. Chin J Org Chem (有机化学). 2018, 38(2): 432-442.
[24] LiuNing (刘宁), Liu Chun(刘春), Jin Zi-lin(金子林). Palladium-catalyzed Suzuki reaction in aqueous media (水相钯催化Suzuki反应) [J]. Chin J Org Chem (有机化学), 2012, 32(5): 860-876.
[25] Niakan M, Asadi Z, Masteri-Farahani M. A covalently anchored Pd(II)-Schiff base complex over a modified surface of mesoporous silica SBA-16: An efficient and reusable catalyst for the Heck-Mizoroki coupling reaction in water [J]. Coll Surf A, 2018, 551: 117-127.
[26] Azaroon M, Kiasat A R. An efficient and new protocol for the Heck reaction using palladium nanoparticle engineered dibenzo-8-crown-6 ether/MCM-41 nanocomposite in water [J]. Appl Org Chem, 2018, 32(4): e4271.
[27] Yang Y,Reber A C, Gilliland III S E, et al. More than just a support: Graphene as a solid-state ligand for palladium catalyzed cross-coupling reactions [J]. J Catal, 2018, 360: 20-26.
[28] Leadbearter N E, Macro M. Transition-metal-free Suzuki-type coupling reactions [J]. Angew Chem Int Ed, 2003, 42(12): 1407-1409.
[29] Kappe C O. Controlled microwave heating in modern organic synthesis [J]. Angew Chem Int Ed, 2004, 43(46): 6250-6284.
[30] Leadbearter N E. Fast, easy, clean chemistry by using water as a solvent and microwave heating: The Suzuki coupling as an illustration [J]. Chem Commun, 2005, 41(23): 2881-2902.
[31] Cui Li-ping (催莉萍), Song Zi-wei (宋子维), Xie Yan-hong (解艳红), et al. Catalytic performance of PAMAM -salicylidene Salen palladium complex for Heck reaction ((聚酰胺-胺树枝状大分子)-水杨醛席夫碱钯配合物的Heck反应催化性能研究)[J]. J Mol Catal (China)(分子催化), 2010, 24(3): 247-253.
[32] Sedighipoor M, Kianfar A H, Mohammadnezhad G, et al. Unsymmetrical palladium(II) N,N,O,O-Schiff base complexes: Efficient catalysts for Suzuki coupling reactions [J]. Inorg Chim Acta, 2018, 476: 20-26.
[33] Jabbari A, Tahmasbi B, Nikoorazm M, et al. A new Pd-Schiff-base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles [J]. Appl Org Chem, 2018, 32(4): e4295.
[34] Sun Bin (孙斌), Wang Jiang-lin(王江淋). Glucose-modified Salen in the application of microwave heating Pd-catalyzed Suzuki reaction in water (葡萄糖修饰的Salen 在微波加热Pd-催化水中的Suzuki 反应中的应用) [J]. Chem Res Appl (化学研究与应用), 2018, 30(9): 1539-1544.
[35] No?l S, Perez F, Pedersen J T, et al. A new water-soluble Cu(II) chelator that retrieves Cu from Cu(amyloid-β) species, stops associated ROS production and prevents Cu(II)-induced Aβ aggregation [J]. J Inorg Biochem, 2012, 117: 322-325.
[2] a. Veerakumar P, Velayudham M, Lu K L, et al. Silica-supported PEI capped nanopalladium as potential catalyst in Suzuki, Heck and Sonogashira coupling reactions [J]. Appl Catal A, 2013, 455: 247-260.b. Cui Feng-juan(崔凤娟), Wang Huan-yu(王环宇), Deng Qing-fang(邓庆芳), et al. Cross-Coupling reaction of aryl halides with grignard reagents catalyzed by nickel complexes supported 2-pyrazolinyl-9-aryl-1, 10-phenanthrolines (2-吡唑啉-9-芳基邻菲咯啉镍配合物催化芳基卤化物和格氏试剂偶联反应的研究) [J]. J Mol Catal(China)(分子催化), 2018, 32(5): 397-404.
[3] Yan Mei(颜美), Feng Xiu-juan(冯秀娟). Advances in Suzuki coupling reactions catalyzed by supported palladium catalysts (负载钯催化的Suzuki偶联反应研究进展) [J]. Chin J Org Chem(有机化学), 2010, 30(5): 623-632.
[4] Danoun K, Essamlali Y, Amadine O, et al. Nanostructured pyrophosphate Na2PdP2O7-catalyzed Suzuki-Mi- yaura cross-coupling under microwave irradiation [J]. Appl Org Chem, 2018, 32(4): e4232.
[5] Shen X, Jones G O, Watson D A, et al. Enantioselective synthesis of axially chiral biaryls by the Pd-catalyzed Suzuki-Miyaura reaction: Substrate scope and quantum mechanical investigations [J]. J Am Chem Soc, 2010, 132(32): 11278-11287.
[6] Felpin F-X, Fouquet E, Zakli C. Improved Suzuki-Miyaura reactions of aryldiazonium salts with boronic acids by tuning palladium on charcoal catalyst properties [J]. Adv Synth Catal, 2009, 351(5): 649-655.
[7] Wu L, Li Z-W, Zhang F, et al. Air-stable and highly active dendritic phosphine oxide-stabilized palladium nano- particles: Preparation, characterization and applications in the carbon-carbon bond formation and hydrogenation reactions [J]. Adv Synth Catal, 2008, 350(6): 846-862.
[8] Manjunatha S G, Rangappa P, Sythana S, et al. A simple way of recycling of homogeneous catalyst in Suzuki reaction [J]. Green Chem Lett Rev, 2013, 6(1): 77-87.
[9] Liu Wen(刘文), Zheng Long-zhen(郑龙珍), Li Yi-di(李引弟). Synthesis of palladium-graphene oxide-Fe3O4 catalyst and its application in Heck reaction (Fe3O4-氧化石墨烯-钯催化剂的制备及其对Heck 反应催化研究) [J]. J Mol Catal (China) (分子催化), 2011, 25(6): 549-556.
[10] Shen Bin(沈彬), Li You (李游), Wang Zhi-fei(王志飞), et al. Catalytic activity of palladium supported on magnetic nanoparticles for Heck reaction (磁性纳米颗粒负载钯催化剂对Heck 反应的催化活性) [J]. Chin J Catal (催化学报), 2007, 28(6): 509-513.
[11] Huang Jin (黄锦), Wang Wei(汪伟). Palladium-tetraphosphine catalyzed Heck coupling reaction (钯和四齿磷配体催化剂应用于Heck反应研究) [J]. J Mol Catal (China) (分子催化), 2018, 32(4): 342-348.
[12] Zhou Y-B, Wang Y-Q,Ning L-C, et al. Conjugated microporous polymer as heterogeneous ligand for highly selective oxidative Heck reaction [J]. J Am Chem Soc, 2017, 139(10): 3966-3969.
[13] Li H J, Wang L. Triethanolamine as an efficient and reusable base, ligand and reaction medium for phosphane-free palladium-katalyzed Heck reactions [J]. Eur J Org Chem, 2006, 2006(22): 5099-5102.
[14] Yu J, Hong Z,Yang X, et al. Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: Synthesis of axitinib [J]. Beilstein J Org Chem 2018, 14(4): 786-795.
[15] Gazvoda M, Virant M, Pinter B, et al. Mechanism of copper-free Sonogashira reaction operates through palladium-palladium transmetallation [J]. Nat Commun, 2018, 9(11): 4814.
[16] Liang B, Dai M, Chen J, et al. Mechanism of copper-free Sonogashira reaction operates through palladium-palladium transmetallation [J]. J Org Chem, 2005, 70(1): 391-393.
[17] Corma A, Huárez R, Boronat M, et al. Gold catalyzes the Sonogashira coupling reaction without the requirement of palladium impurities [J]. Chem Commun, 2011, 47(5): 1446-1448.
[18] Cheng J, Sun Y, Wang F, et al. A copper- and amine-free Sonogashira reaction employing aminophosphines as ligands [J]. J Org Chem, 2004, 69(16): 5428-5432.
[19] Li Hong-lin(李红玲), Zhang Xia(张霞), Lin Hong-tao(蔺红桃), et al. Phosphine free, copper free palladium catalyzed Sonogashira cross-coupling reactions in ionic liquids (离子液体中无磷、无铜、钯催化的Sonogashira交联反应研究) [J]. J Mol Catal (China) (分子催化), 2009, 23(5): 412-417.
[20] Gholinejad M, Bahrami M, Najera C, et al. Magnesium oxide supported bimetallic Pd/Cu nanoparticles as an efficient catalyst for Sonogashira reaction [J]. J Catal, 2018, 363: 81-91.
[21] Beletskaya I P, Cheprakov A V. The Heck reaction as a sharpening stone of palladium catalysis [J]. Chem Rev, 2000, 100(8): 3009-3066.
[22] Dounay A B, Overman L E. The asymmetric intramolecular Heck reaction in natural product total synthesis [J]. Chem Rev, 2003, 103(8): 2954-2963.
[23] KongSheng-nan(孔胜男), Malik A U, Qian Xue-feng(钱雪峰), et al. C-C coupling reactions in water catalyzed by palladium(II) supported on microporous organic polymer (水相中微孔有机聚合物负载钯催化的碳-碳偶联反应) [J]. Chin J Org Chem (有机化学). 2018, 38(2): 432-442.
[24] LiuNing (刘宁), Liu Chun(刘春), Jin Zi-lin(金子林). Palladium-catalyzed Suzuki reaction in aqueous media (水相钯催化Suzuki反应) [J]. Chin J Org Chem (有机化学), 2012, 32(5): 860-876.
[25] Niakan M, Asadi Z, Masteri-Farahani M. A covalently anchored Pd(II)-Schiff base complex over a modified surface of mesoporous silica SBA-16: An efficient and reusable catalyst for the Heck-Mizoroki coupling reaction in water [J]. Coll Surf A, 2018, 551: 117-127.
[26] Azaroon M, Kiasat A R. An efficient and new protocol for the Heck reaction using palladium nanoparticle engineered dibenzo-8-crown-6 ether/MCM-41 nanocomposite in water [J]. Appl Org Chem, 2018, 32(4): e4271.
[27] Yang Y,Reber A C, Gilliland III S E, et al. More than just a support: Graphene as a solid-state ligand for palladium catalyzed cross-coupling reactions [J]. J Catal, 2018, 360: 20-26.
[28] Leadbearter N E, Macro M. Transition-metal-free Suzuki-type coupling reactions [J]. Angew Chem Int Ed, 2003, 42(12): 1407-1409.
[29] Kappe C O. Controlled microwave heating in modern organic synthesis [J]. Angew Chem Int Ed, 2004, 43(46): 6250-6284.
[30] Leadbearter N E. Fast, easy, clean chemistry by using water as a solvent and microwave heating: The Suzuki coupling as an illustration [J]. Chem Commun, 2005, 41(23): 2881-2902.
[31] Cui Li-ping (催莉萍), Song Zi-wei (宋子维), Xie Yan-hong (解艳红), et al. Catalytic performance of PAMAM -salicylidene Salen palladium complex for Heck reaction ((聚酰胺-胺树枝状大分子)-水杨醛席夫碱钯配合物的Heck反应催化性能研究)[J]. J Mol Catal (China)(分子催化), 2010, 24(3): 247-253.
[32] Sedighipoor M, Kianfar A H, Mohammadnezhad G, et al. Unsymmetrical palladium(II) N,N,O,O-Schiff base complexes: Efficient catalysts for Suzuki coupling reactions [J]. Inorg Chim Acta, 2018, 476: 20-26.
[33] Jabbari A, Tahmasbi B, Nikoorazm M, et al. A new Pd-Schiff-base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles [J]. Appl Org Chem, 2018, 32(4): e4295.
[34] Sun Bin (孙斌), Wang Jiang-lin(王江淋). Glucose-modified Salen in the application of microwave heating Pd-catalyzed Suzuki reaction in water (葡萄糖修饰的Salen 在微波加热Pd-催化水中的Suzuki 反应中的应用) [J]. Chem Res Appl (化学研究与应用), 2018, 30(9): 1539-1544.
[35] No?l S, Perez F, Pedersen J T, et al. A new water-soluble Cu(II) chelator that retrieves Cu from Cu(amyloid-β) species, stops associated ROS production and prevents Cu(II)-induced Aβ aggregation [J]. J Inorg Biochem, 2012, 117: 322-325.