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
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Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
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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.