Distinct roles of Ag(I) and Cu(II) as cocatalysts in the intramolecular cyclization of N-methyl-N-phenylanthranilic acid: A theoretical investigation

Molecular Catalysis - Tập 509 - Trang 111634 - 2021
Jiaying Sun1,2, Shaojing Liu2, Lingli Han1,2, Tao Liu1,2
1Department of Chemistry and Chemical Engineering, Jining University, Qufu 273155, Shandong, China
2School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China

Tài liệu tham khảo

Huang, 2020, Redox-neutral decarboxylative photocyclization of anthranilic acids, Green Chem., 22, 8243, 10.1039/D0GC02789H Chavan, 2016, Carbonylation of anthranilic acid with aryl and heteroaryl bromides to synthesize benzoxazinone derivatives, Asian J. Org. Chem., 5, 1120, 10.1002/ajoc.201600253 Karapetyan, 2020, Interaction of 2-imino-2, 5-dihydrofuran-3-carboxamides with anthranilic acid, Russ. J. Org. Chem., 56, 1484, 10.1134/S1070428020080217 Jahan, 2018, Anthranilic acid derivatives: novel inhibitors of protein glycation and the associated oxidative stress in the hepatocytes, Med. Chem., 14, 516, 10.2174/1573406413666171020120528 Hussaini, 2016, New polymeric based materials: terpoly (aniline, diphenyl amine, and o-anthranilic acid)/kaolinite composites, Polym. Adv. Technol., 27, 1604, 10.1002/pat.3837 Sharma, 2002, Newer N-substituted anthranilic acid derivatives as potent anti-inflammatory agents, Eur. J. Med. Chem., 37, 689, 10.1016/S0223-5234(02)01340-5 Rai, 2018, Green synthesis, crystal growth, and some physicochemical studies on an inter-molecular compound of anthranilic acid and m-nitro-benzoic acid system, J. Therm. Anal. Calorim., 134, 1001, 10.1007/s10973-018-7344-2 Kang, 2020, Transition-metal-catalyzed C-H functionalization of pyrazoles, Org. Biomol. Chem., 18, 6192, 10.1039/D0OB01265C Li, 2020, Recent advances in using transition-metal-catalyzed C-H functionalization to build fluorescent materials, Chem, 10, 2591, 10.1016/j.chempr.2020.08.017 Lapuh, 2020, Chiral transient directing groups in transition-metal-catalyzed enantioselective C-H bond functionalization, ACS Catal., 10, 12898, 10.1021/acscatal.0c03317 Jiang, 2016, Advances in theoretical study on transition-metal-catalyzed C-H activation, Sci. China: Chem., 59, 1448, 10.1007/s11426-016-0330-3 Polák, 2020, Formal transition-metal-catalyzed phosphole C-H activation for the synthesis of pentasubstituted phospholes, Org. Lett., 22, 2187, 10.1021/acs.orglett.0c00359 Wang, 2015, Directing group-assisted transition-metal-catalyzed vinylic C-H bond functionalization, Sci. China: Chem., 58, 1252, 10.1007/s11426-015-5362-5 Mo, 2015, Transition-metal-catalyzed direct C-H functionalization under external-oxidant-free conditions, Synthesis (Mass), 47, 439, 10.1055/s-0034-1379890 Li, 2021, Transition-metal-catalyzed intermolecular C-H carbonylation toward amides, Synlett, 32, 07, 10.1055/s-0040-1706416 Kumar, 2020, Transition metal-catalyzed coupling of heterocyclic alkenes via C-H functionalization: recent trends and applications, Org. Chem. Front., 7, 1527, 10.1039/D0QO00279H Pollice, 2019, A universal quantitative descriptor of the dispersion interaction potential, Angew. Chem. Int. Ed., 58, 9758, 10.1002/anie.201905439 Pirgheibi, 2021, Density functional theory study of the interplay between cation–π and intramolecular hydrogen bonding interactions in complexes involving methyl salicylate with Li+, Na+, K+, Be2+, Mg2+, Ca2+cations, Comput. Theor. Chem., 1198, 10.1016/j.comptc.2021.113172 Utenyshev, 2001, X-ray diffraction analysis and luminescence spectral study of crystal solvates of N-(N"-tosylanthranoyl) anthranilic acid with acetic acid and dimethylformamide, Russ. Chem. Bull., 50, 728, 10.1023/A:1011389601879 Hu, 2019, Pd-catalyzed intramolecular chemoselective C(sp2)-H and C(sp3)-H activation of N-alkyl-N-arylanthranilic acids, Org. Lett., 21, 989, 10.1021/acs.orglett.8b03976 Lu, 2013, An improved B3LYP method in the calculation of organic thermochemistry and reactivity, Comput. Theor. Chem., 1015, 64, 10.1016/j.comptc.2013.04.009 Caldeira, 2019, Partial combination of composite strategy and the B3LYP functional for the calculation of enthalpies of formation, J. Mol. Model., 25, 1, 10.1007/s00894-019-3952-4 Hickert, 2011, A B3LYP investigation of the conformational and environmental sensitivity of carbon-deuterium frequencies of aryl-perdeuterated phenylalanine and tryptophan, Theor. Chem. Acc., 130, 883, 10.1007/s00214-011-1050-5 Broda, 2012, Anharmonic vibrational frequency calculations for solvated molecules in the B3LYP Kohn-Sham basis set limit, Vib. Spectrosc., 63, 432, 10.1016/j.vibspec.2012.09.005 Mahadevan, 2011, FT-IR and FT-Raman, UV spectroscopic investigation of 1-bromo-3-fluorobenzene using DFT (B3LYP, B3PW91 and MPW91PW91) calculations, Spectrochim. Acta, Part A, 82, 481, 10.1016/j.saa.2011.07.082 Matczak, 2012, Assessment of B3LYP combined with various ECP basis sets for systems containing Pd, Sn, and Pb, Comput. Theor. Chem., 983, 25, 10.1016/j.comptc.2011.12.023 Check, 2001, Addition of polarization and diffuse functions to the LanL2DZ basis set for p-block elements, J. Phys. Chem. A, 105, 8111, 10.1021/jp011945l Khajehzadeh, 2017, Molecular structure, FT-IR, NMR, UV, NBO and HOMO-LUMO of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile by DFT/B3LYP and PBEPBE methods with LanL2DZ and 6-311++G(d,2p) basis sets, Spectrochim. Acta, Part A, 180, 51, 10.1016/j.saa.2017.02.055 Yang, 2009, Assessment of the “6-31+G**+LanL2DZ” mixed basis set coupled with density functional theory methods and the effective core potential: prediction of heats of formation and ionization potentials for first-row-transition-metal complexes, J. Phys. Chem. A, 113, 9843, 10.1021/jp807643p Maeda, 2015, Intrinsic reaction coordinate: calculation, bifurcation, and automated search, Int. J. Quantum Chem., 115, 258, 10.1002/qua.24757 Fukui, 1981, The path of chemical reactions-the IRC approach, Acc. Chem. Res., 14, 363, 10.1021/ar00072a001 Taketsugu, 1995, Dynamic reaction path analysis based on an intrinsic reaction coordinate, J. Chem. Phys., 103, 10042, 10.1063/1.470704 Yoshizawa, 1999, Intrinsic reaction coordinate analysis of the conversion of methane to methanol by an iron-oxo species: a study of crossing seams of potential energy surfaces, J. Chem. Phys., 111, 538, 10.1063/1.479333 Jacquemin, 2010, On the performances of the M06 family of density functionals for electronic excitation energies, J. Chem. Theory Comput., 6, 2071, 10.1021/ct100119e Wheeler, 2010, Integration grid errors for meta-GGA-predicted reaction energies: origin of grid errors for the M06 suite of functionals, J. Chem. Theory Comput., 6, 395, 10.1021/ct900639j Walker, 2013, Performance of M06, M06-2X, and M06-HF density functionals for conformationally flexible anionic clusters: M06 functionals perform better than B3LYP for a model system with dispersion and ionic hydrogen-bonding interactions, J. Phys. Chem., 117, 12590, 10.1021/jp408166m Wang, 2018, Revised M06 density functional for main-group and transition-metal chemistry, Proc. Natl. Acad. Sci., 115, 10257, 10.1073/pnas.1810421115 Sutton, 2012, First principles pKa calculations on carboxylic acids using the SMD solvation model: effect of thermodynamic cycle, model chemistry, and explicit solvent molecules, J. Chem. Phys. B, 116, 11999, 10.1021/jp305876r Marenich, 2009, Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions, J. Chem. Phys. B, 113, 6378, 10.1021/jp810292n Igel-Mann, 1988, Pseudopotentials for main group elements (IIIa through VIIa), Mol. Phys., 65, 1321, 10.1080/00268978800101811 Frisch, 2009 Legault, 2009 Poater, 2005, Theoretical evaluation of electron delocalization in aromatic molecules by means of atoms in molecules (AIM) and electron localization function (ELF) topological approaches, Chem. Rev., 105, 3911, 10.1021/cr030085x Kumar, 2016, Bader's theory of atoms in molecules (AIM) and its applications to chemical bonding, J. Chem. Sci., 128, 1527, 10.1007/s12039-016-1172-3 Volkov, 2000, Evaluation of net atomic charges and atomic and molecular electrostatic moments through topological analysis of the experimental charge density, Acta Crystallogr. Sect. A, 56, 252, 10.1107/S0108767300001628 Molina, 2001, The three-center-four-electron (3c-4e) bond nature revisited. An atoms-in-molecules theory (AIM) and ELF study, Theor. Chem. Acc., 105, 328, 10.1007/s002140000231 Contreras-García, 2011, NCIPLOT: a program for plotting noncovalent interaction regions, J. Chem. Theory Comput., 7, 625, 10.1021/ct100641a Lu, 2012, Multiwfn: a multifunctional wavefunction analyzer, J. Comput. Chem., 33, 580, 10.1002/jcc.22885 Lu, 2012, Quantitative analysis of molecular surface based on improved Marching Tetrahedra algorithm, J. Mol. Graphics Modell., 38, 314, 10.1016/j.jmgm.2012.07.004 Shimoyama, 2020, Mechanistic study of Pd/Ag dual-catalyzed cross-dehydrogenative coupling of perfluoroarenes with thiophenes, ACS Catal., 10, 3390, 10.1021/acscatal.9b05326 Sajjad, 2018, NBO orbital interaction analysis for the ambiphilic metal-ligand activation/concerted metalation deprotonation (AMLA/CMD) mechanism involved in the cyclopalladation reaction of N,N-dimethylbenzylamine with palladium acetate, Organometallics, 37, 3659, 10.1021/acs.organomet.8b00303 Kanazawa, 2020, Pd/Cu-catalyzed dehydrogenative coupling of dimethyl phthalate: synchrotron radiation sheds light on the Cu cycle mechanism, ACS Catal., 10, 5909, 10.1021/acscatal.0c00918 Sha, 2018, Cation-π interactions in the benzylic arylation of toluenes with bimetallic catalysts, J. Am. Chem. Soc., 140, 12415, 10.1021/jacs.8b05143 Zhang, 2016, Positional selectivity in C-H functionalizations of 2-benzylfurans with bimetallic catalysts, J. Am. Chem. Soc., 138, 4260, 10.1021/jacs.6b01578 Zhang, 2014, NiXantphos: a deprotonatable ligand for room-temperature palladium-catalyzed cross-couplings of aryl chlorides, J. Am. Chem. Soc., 136, 6276, 10.1021/ja411855d Meyer, 2003, Interactions with aromatic rings in chemical and biological recognition, Angew. Chem. Int. Ed., 42, 1210, 10.1002/anie.200390319