Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction
- Corresponding author: Min WANG, wangmin@qymail.bhu.edu.cn
Citation: Yingchun ZHANG, Yiwei SHI, Ruijie YANG, Xin WANG, Zhiguo SONG, Min WANG. Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
Pu M X, Guo H Y, Quan Z S, Li X T, Shen Q K. Application of the Mannich reaction in the structural modification of natural products[J]. J. Enzym. Inhib. Med. Chem., 2023,38(1):1-18.
Kulkarni P. Sulfanilic acid catalysed one-pot three-component Mannich reaction for synthesis of β-amino ketones[J]. Vietnam J. Chem., 2020,58(5):675-687. doi: 10.1002/vjch.202000090
Rani P, Prakash M, Samanta S. Organobase-catalyzed Mannich reaction of cyclic N-sulfonyl imines and 1, 2-diketones: A sustainable approach to 4-(3-arylquinoxalin-2-ylmethyl) sufamidates[J]. Tetrahedron Lett., 2023,122154490. doi: 10.1016/j.tetlet.2023.154490
Mohurle S, Pasuparthy S D, Talamarla D, Kali V, Maiti B. [BCMIM][Cl] ionic liquid catalyzed diastereoselective synthesis of β-amino ketones via facile, one-pot, multicomponent Mannich reaction under solvent-free condition[J]. J. Heterocycl. Chem., 2023,60(9):1545-1557. doi: 10.1002/jhet.4698
Azizi N, Edrisi M. Deep eutectic solvent immobilized on SBA-15 as a novel separable catalyst for one-pot three-component Mannich reaction[J]. Microporous Mesoporous Mat., 2017,240(11):130-136.
Kalhor H R, Piraman Z, Fathali Y. Hen egg white lysozyme encapsulated in ZIF-8 for performing promiscuous enzymatic Mannich reaction[J]. iScience, 2023,26(10):1-21.
Yang Z N, He H K, Tian R, Wu R R, Hu S, Wu Y, Zhou H. A zinc/ PyBisulidine catalyzed asymmetric Mannich reaction of N-tosyl imines with 3-acyloxy-2-oxindoles[J]. Org. Biomol. Chem., 2021,19(34):7460-7469. doi: 10.1039/D1OB01328A
Mote N R, Chikkali S H. Hydrogen-bonding-assisted supramolecular metal catalysis[J]. Chem. Asian J., 2018,13(23):3623-3646. doi: 10.1002/asia.201801302
Deng J H, Luo J, Mao Y L, Lai S, Gong Y N, Zhong D C, Lu T B. π-π stacking interactions: Non-negligible forces for stabilizing porous supramolecular frameworks[J]. Sci. Adv., 2020,6(2)eaax9976. doi: 10.1126/sciadv.aax9976
Wang Y J, Wang M Y, Li Y B, Liu Q. Homogeneous manganese- catalyzed hydrogenation and dehydrogenation reactions[J]. Chem, 2021,7(5):1180-1223. doi: 10.1016/j.chempr.2020.11.013
Liu C G, Wang M Y, Liu S H, Wang Y J, Peng Y, Lan Y, Liu Q. Manganese-catalyzed asymmetric hydrogenation of quinolines enabled by π-π interaction[J]. Angew. Chem. Int. Ed., 2021,60(10):5108-5113. doi: 10.1002/anie.202013540
Zhang D P, Lan W L, Zhou Z, Yang L, Liu Q Y, Bian Y Z, Jiang J Z. Manganese(Ⅲ) porphyrin-based magnetic materials[J]. Top. Curr. Chem., 2019,377(18):1-43.
Tao P, Liu S J, Wong W Y. Phosphorescent manganese(Ⅱ) complexes and their emerging applications[J]. Adv. Opt. Mater., 2020,8(20)2000985. doi: 10.1002/adom.202000985
QI J Y, DANG X Y, ZHANG Y C, SONG Z G, WANG M. Study on the structure and catalytic property of two copper benzenesulfonate complexes[J]. Chemical Research and Application, 2022,34(11):2610-2618. doi: 10.3969/j.issn.1004-1656.2022.11.003
Lin R B, Chen B. Hydrogen-bonded organic frameworks: Chemistry and functions[J]. Chem, 2022,8(8):2114-2135. doi: 10.1016/j.chempr.2022.06.015
Bruker. SMART (Version 5.628), SAINT (Version 6.45), and SADABS. Bruker AXS Inc. : Madison, WI, 2001.
Sheldrick G M. SHELXL-97, Program for the refinement of crystal structures. University of Göttingen, Germany, 1997.
Wang C P, Wang Z, Mao S J, Chen Z R, Wang Y. Coordination environment of active sites and their effect on catalytic performance of heterogeneous catalysts[J]. Chin. J. Catal., 2022,43(4):928-955. doi: 10.1016/S1872-2067(21)63924-4
Xie C, Yan D F, Li H, Du S Q, Chen W, Wang Y Y, Zou Y Q, Chen R, Wang S Y. Defect chemistry in heterogeneous catalysis: Recognition, understanding, and utilization[J]. ACS Catal., 2020,10(19):11082-11098. doi: 10.1021/acscatal.0c03034
Han B, Wang H L, Wang C M, Wu H, Zhou W, Chen B L, Jiang J Z. Postsynthetic metalation of a robust hydrogen-bonded organic framework for heterogeneous catalysis[J]. J. Am. Chem. Soc., 2019,141(22):8737-8740. doi: 10.1021/jacs.9b03766
XIA X, WANG S, YANG X Q, FAN R, WEI R Z, LIU Z, TANG Q. Synthesis, crystal structure and properties of zinc complex based on 2, 5-bis(trifluoromethyl) terephthalic acid ligand[J]. Chinese J. Inorg. Chem., 2021,37(12):2133-2140. doi: 10.11862/CJIC.2021.254
Vassileva P, Krastev V, Lakov L, Peshev O. XPS determination of the binding energies of phosphorus and nitrogen in phosphazenes[J]. J. Mater. Sci., 2004,39(9):3201-3202. doi: 10.1023/B:JMSC.0000025859.82714.4a
Neuvonen H, Neuvonen K, Koch A, Kleinpeter E, Pasanen P. Electron-withdrawing substituents decrease the electrophilicity of the carbonyl carbon. An investigation with the aid of 13C NMR chemical shifts, ν(C=O) frequency values, charge densities, and isodesmic reactions to interprete substituent effects on reactivity[J]. J. Org. Chem., 2002,67(20):6995-7003. doi: 10.1021/jo020121c
Rakhtshah J, Ghaderi H, Yaghoobi F, Baghery S, Shaabani B. Synthesis of α-aminoalkyl naphthol derivatives in the presence of nickel complexes immobilized on multi-wall carbon nanotubes[J]. Mater. Chem. Phys., 2020,239121985. doi: 10.1016/j.matchemphys.2019.121985
Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two LnⅢ3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
Shuyan ZHAO . Field-induced CoⅡ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO2-0.39IrOx composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo2O4/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO2 reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
Symmetry code: 1-x, 1-y, 1-z.
Reaction conditions: 10 mmol of 2-naphthol, 10 mmol of benzaldehyde, 11 mmol of benzamide, 0.1 mmol of complex 1 or 2, 95 ℃, solvent-free.