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Research Article

Development of mixed-ligand ruthenium complexes bearing phosphine and imine ligands for utilisation as catalysts in Suzuki-type C–C cross-coupling reactions

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Received 19 Feb 2024, Accepted 04 May 2024, Published online: 03 Jun 2024

References

  • Qi X, Li Y, Bai R, et al. Mechanism of rhodium-catalyzed C–H functionalization: advances in theoretical investigation. Acc. Chem. Res. 2017;50:2799–2808. doi:10.1021/acs.accounts.7b00400
  • Singh KS. Recent advances in C–H bond functionalization with ruthenium-based catalysts. Catalysts. 2019;9:173. doi:10.3390/catal9020173
  • Khake SM, Chatani N. Chelation-assisted nickel-catalyzed C−H functionalizations. Trends Chem. 2019;1:524–539. doi:10.1016/j.trechm.2019.06.002
  • He Y, Huang Z, Wu K, et al. Recent advances in transition-metal-catalyzed carbene insertion to C–H bonds. Chem. Soc. Rev. 2022;51:2759–2852. doi:10.1039/D1CS00895A
  • Henrion M, Ritleng V, Chetcuti MJ. Nickel N-heterocyclic carbene-catalyzed C–C bond formation: reactions and mechanistic aspects. ACS Catal. 2015;5:1283–1302. doi:10.1021/cs5014927
  • Kramer S. Homogeneous gold-catalyzed aryl-aryl coupling reactions. Synthesis (Mass). 2020;52:2017–2030. doi:10.1055/s-0039-1690882
  • Arora V, Narjinari H, Nandi PG, et al. Recent advances in pincer–nickel catalyzed reactions. Dalton Trans. 2021;50:3394–3428. doi:10.1039/D0DT03593A
  • Naskar R, Majumder A, Kundu K, et al. Palladium(II) complexes bearing a mixed set of aNHC/Py/PR3/I2 ligands: applications in α-arylation of amide and Suzuki-Miyaura coupling reactions. J. Organomet. Chem. 2021;949:121925. doi:10.1016/j.jorganchem.2021.121925
  • Majumder A, Saha TN, Majumder N, et al. Heterobimetallic carbene complexes bearing cyclometalated IrIII/RhIII and mixed NHC^Py/PPh3 coordinated PdII centers: structures and tandem catalysis. Eur. J. Inorg. Chem. 2021: 1104–1110. doi:10.1002/ejic.202001080
  • Dey BK, Dutta J, Drew MGB, et al. Chloro-ruthenium complexes with carbonyl and N-(aryl)pyridine-2-aldimines as ancillary ligands. synthesis, characterization and catalytic application in C–C cross-coupling of arylaldehydes with arylboronic acids. J. Organomet. Chem. 2014;750:176–184. doi:10.1016/j.jorganchem.2013.11.019
  • Mukherjee A, Hrovat DA, Richmond MG, et al. A new diphosphine-carbonyl complex of ruthenium: an efficient precursor for C–C and C–N bond coupling catalysis. Dalton Trans. 2018;47:10264–10272. doi:10.1039/C8DT01085D
  • Yang SP, Chen XM, Ji LN. Influence of the counter ions and ligands on structures of silver(I) helicates with di-Schiff bases containing imidazole groups. J. Chem. Soc. Dalton Trans. 2000: 2337–2344. doi:10.1039/b002837l
  • Wang C, Wu C, Feng P, et al. Synthesis and biological activities of metal complexes with Schiff Base ligand derived from imidazole-2-carboxaldehyde and ethylenediamine. Lat. Am. J. Pharm. 2017;36:1169–1176.
  • Bréfuel N, Shova S, Tuchagues JP. FeII bistable materials with dissymmetrical ligands: synthesis, crystal structure, magnetic and Mössbauer properties of FeII complexes based on N4 schiff bases possessing 2-Pyridyl and 1-R-Imidazol-2-yl rings. Eur. J. Inorg. Chem. 2007: 4326–4334. doi:10.1002/ejic.200700320
  • Dominguez-Vera JM, Camara F, Moreno JM, et al. A pro-chiral bis-imidazolyl-containing copper(II) complex as precursor of a self-assembled polymer and a heterodinuclear copper(II)-nickel(II) complex. Inorg Chim Acta. 2000;306:137–141.
  • Dominguez-Vera JM, Camara F, Moreno JM, et al. A new mononuclear copper(II) complex containing two imidazolyl moieties as precursor to self-assembled and NiIICuIINiII heterobimetallic complexes. Inorg. Chem. 1998;37:3046–3050.
  • Saha R, Mukherjee A, Bhattacharya S. Di-ruthenium complexes of 1, 4-diazabutadiene ligands: synthesis, characterization and utilization as catalyst-precursor for oxidative coupling of amine to imine in air, New J. Chem. 2023;47:12709–12717.
  • Paul P, Seth DK, Richmond MG, et al. Unusual chemical transformations of acetone thiosemicarbazone mediated by ruthenium: C–H bond activation, thiolation, and C–N bond cleavage. RSC Adv. 2014;4:1432–1440. doi:10.1039/C3RA44329A
  • Sen J, Paul P, Chowdhury NS, et al. 1-Nitroso-2-naphtholate complexes of ruthenium (II): synthesis, isomerization and, spectral and electrochemical properties. J. Indian Chem. Soc. 2014;91:1089–1097.
  • Stephenson TA, Wilkinson G. New complexes of ruthenium (II) and (III) with triphenylphosphine, triphenylarsine, trichlorostannate, pyridine and other ligands. J. Inorg. Nucl. Chem. 1966;28:945–956. doi:10.1016/0022-1902(66)80191-4
  • Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, revision E.01. Wallingford (CT): Gaussian, Inc.; 2009.
  • Chemical shifts for the NMR data are given in ppm; multiplicity of the signals along with the associated coupling constant and number of hydrogen(s) are given in parentheses; overlapping signals are marked with an asterisk (*).
  • Sheldrick GM. SHELXS-97 and SHELXL-97, Fortran programs for crystal structure solution and refinement. Göttingen: University of Göttingen; 1997.
  • Sheldrick GM. A short history of SHELX. Acta Crystallogr. Sect. A. 2008;64:112–122.
  • Yield of the desired product decreases significantly in the absence of NEt3.
  • Chandra A, Dhibar P, Dutta P, et al. N-(Aryl)pyrrole-2-aldimine complexes of ruthenium: synthesis, structure, and spectral and electrochemical properties. New J. Chem. 2023;47:3492–3501.
  • Saha R, Mukherjee A, Bhattacharya S. Development of a ruthenium–aquo complex for utilization in synthesis and catalysis for selective hydration of nitriles and alkynes. New J. Chem. 2022;46:9098–9110.
  • The same optimized condition, as in the reactions with aryl iodides, was used.
  • The imine ligand probably gets protonated, and behaves as a bidentate diimine ligand (as shown in Scheme 1).
  • Akiyama T, Taniguchi T, Saito N, et al. Ligand-free Suzuki–Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system. Green Chem. 2017;19:3357–3369. doi:10.1039/C7GC01166K

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