Abstract
The preparation and characterization of a series of new 2-phenylpyridine derivative ligands consisting of 2-(R) pyridine (R = mesityl (L1), 2,6-dimethylphenyl (L2), o-tolyl (L3), m-tolyl (L4), p-tolyl (L5), o-methoxyphenyl (L6), and p-methoxyphenyl (L7)) and their Pd complexes [PdCl2L2] (L1–L7) is investigated using a combination of X-ray diffraction spectroscopy, GC-MS, and NMR. The crystal structures show that the Pd complexes adopt a square planar geometry, and the monodentate ligand is coordinated through the N donor of the pyridine ring to the Pd atom. The catalytic activities of the synthesized complexes are investigated. The square planar Pd complex trans-[(2-mesitylpy)2PdCl2)] shows a high efficiency in promoting Suzuki-Miyaura cross coupling in an aqueous solvent under aerobic conditions.
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References
Handbook of OrganoPd Chemistry for Organic Synthesis/Ed. E.-i Negishi.; Wiley-Interscience: New York, 2002.
N. Miyaura. Cross-Coupling Reactions: A Practical Guide. Springer: New York, 2002.
A. Suzuki and H. C. Brown. Organic Synthesis via Boranes. Aldrich Chemical Co: Milwaukee, WI, 2002, 3.
A. Suzuk. Angew. Chem. Int., Ed., 2011, 50, 6722–6737.
H. Valdés, D. Canseco-González, J. M. Germán-Acacio, and D. Morales-Morales. J. Organomet. Chem., 2018, 867, 51.
K. O. Marichev, S. A. Patil, and A. Bugarin. Tetrahedron, 2018, 74, 2523.
Y. Zhang and G. Lavigne. Eur. J. Inorg. Chem., 2015, 2042–2050.
M. E. Hanhan. Appl. Organomet. Chem., 2008, 22, 270–275.
Y. Lai, Z. Zong, Y. Tang, W. Mo, N. Sun, B. Hu, Z. Shen, L. Jin, W. Sun, and X. Hu. Beilstein J. Org. Chem., 2017, 13, 213–221.
S. Ghosh, A. S. Kumar, and G. N. Mehta. Beilstein J. Org. Chem., 2010, 4, 4–7.
L. J. Goossen and B. Melzer. J. Org. Chem., 2007, 7473–7476.
H. Khojasteh, V. Mirkhani, M. Moghadam, S. Tangestaninejad, and I. Mohammadpoor-Baltork. J. Nano Struct., 2015, 5, 271.
I. Maluenda and O. Navarro. Molecules, 2015, 20, 7528.
Y.-N. Yu and M.-H. Xu. Acta Chim. Sin., 2017, 75, 655–670.
R. E. Andrew, L. Gonzalez-Sebastian, and A. B. Chaplin. Dalton Trans., 2016, 45, 1299–1305.
A. Fihri, P. Meunier. and J. Hierso. Coord. Chem. Rev., 2007, 251, 2017–2055.
W. A. Herrmann and C. Köcher. Angew. Chem., Int. Ed. Engl., 1997, 36, 2162.
D. Bourissou, O. Guerret, F. P. Gabbaï, and G. Bertrand. Chem. Rev., 2000, 100, 39.
I. J. B. Lin and C. S. Vasam. Coord. Chem. Rev., 2007, 251, 642–670.
C. E. Willans, K. M. Anderson, M. J. Paterson, P. C. Junk, L. J. Barbour, and J. W. Steed. Eur. J. Inorg. Chem., 2009, 2835.
Z. Guan, J. Hu, Y. Gu, H. Zhang, G. Li, and T. Li. Angew. Chem., Int. Ed., 2006, 45, 1282–1284.
Z. Z. Zhou, F. S. Liu, D. S. Shen, C. Tan, and L. Y. Luo. Inorg. Chem. Commun., 2011, 14, 659.
I. D. Kostas, A. G. Coutsolelos, G. Charalambidis, and A. Skondra. Tetrahedron Lett., 2007, 48, 6688–6691.
D. H. Lee and M. J. Jin. Org. Lett., 2011, 13, 252–255.
E. Amadio, M. Bertoldini, A. Scrivanti, G. Chessa, V. Beghetto, U. Matteoli, R. Bertani, and A. Dolmella. Inorg. Chim. Acta, 2011, 370, 388–393.
E. Amadio, A. Scrivanti, G. Chessa, U. Matteoli, V. Beghetto, M. Bertoldini, M. Rancan, A. Dolmella, A. Venzo, and R. Bertani. J. Organomet. Chem., 2012, 716, 193–200.
P. Liu, M. Yan, and R. He. Appl. Organomet. Chem., 2010, 24, 131–134.
L. Shen, S. Huang, Y. Nie, and F. Lei. Molecules, 2013, 18, 1602–1612.
V. Montoya, J. Pons, V. Branchadell, J. Garcia-Antón, X. Solans, M. Font-Bardia, and J. Ros. Organometallics, 2008, 27, 1084–1091.
J. A. Perez, J. Pons, X. Solans, M. Font-Bardia, and J. Ros. Inorg. Chim. Acta, 2005, 358, 617–622.
I. A. Mkhalid and H. F. Al-shaikh. Asian J. Chem., 2014, 26, 2077–2082.
A. Suzuki. In: Handbook of OrganoPd Chemistry for Organic Synthesis/Ed. E.-i. Negishi. Wiley Interscience: New-York, 2002, Ch. III.2.2.
J. C. Anderson, H. Namli, and C. A. Roberts. Tetrahedron, 1997, 53, 15123–15134.
H. Tatamidani, F. Kakiuchi, and N. Chatani. Org. Lett., 2004, 6, 3597–3599.
G. A. Anderson and M. Lie. Inorg. Synthesis, 1990, 28, 61.
Agilent. CrysAlis PRO. Agilent Technologies, Yarnton, England, 2012.
G. M. Sheldrick. SHELXS, SHELXL. Acta Crystallogr., 2008, A64, 112.
L. J. Barbour. J. Supramol. Chem., 2001, 1, 189.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann. J. Appl. Crystallogr., 2009, 42, 339–341.
C. A. Tolman. Chem. Rev., 1977, 77, 313–348.
A. de Meijere, F. Diederich. Metal-catalyzed Cross-coupling Reactions. Wiley-VCH: Weinheim, 2004.
N. J. Whitcome, K. K. Hii, and S. E. Gibson. Tetrahedron, 2001, 57, 7449–7476.
Acknowledgments
The authors acknowledge DSR for technical and financial support. Abdulmuizz Adamson is thankful to King Abdulaziz University for providing a scholarship.
Funding
This project was funded by the Deanship of Scientific Research (DSR) at King Abdulaziz University, Jeddah, under grant no. 1438/130/227.
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Text © The Author(s), 2020, published in Zhurnal Strukturnoi Khimii, 2020, Vol. 61, No. 3, pp. 489–497.
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Adamson, A., Budiman, Y.P., Mkhalid, I. et al. Palladium (II) Complexes Containing 2-Phenylpyridine Derivatives: Synthesis, Molecular Structures, and Catalytic Activity for Suzuki–Miyaura Cross-Coupling Reactions. J Struct Chem 61, 466–475 (2020). https://doi.org/10.1134/S0022476620030130
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DOI: https://doi.org/10.1134/S0022476620030130