Abstract
Electrochemical dissolution of sacrificial Pd anode was used to synthesize novel polynuclear PdII complexes with ligands based on polyamic acids containing in the main chain biquinolyl groups capable of coordination to the metal ions. The synthesized polymeric complexes exhibit high catalytic activity in the Suzuki reaction. The reaction can be run under mild conditions, at 40 °C and with a sufficiently high product yield at a catalyst concentration of 0.05 mol.% (with respect to the starting aryl halide). The polymeric ligand allows immobilization of the catalyst on the graphite fabric with high specific surface area that enhances the catalyst turnover number and promotes its recycling.
Similar content being viewed by others
References
N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.
F. Alonso, I. P. Beletskaya, and M. Yus, Tetrahedron, 2008, 64, 3047.
J. Corbet and G. Mignani, Chem. Rev., 2006, 106, 2651.
H. Chiong and O. Daugulis, Org. Lett., 2007, 9, 1449.
S. E. Denmark and M. E. Schnute, J. Org. Chem., 1995, 60, 1013.
B.M. Choudary, S. Madhi, N.S. Chowdari, M. L. Kantam, and B. Sreedhar, J. Am. Chem. Soc., 2002, 124, 14127.
S. Klingelho, W. Heitz, A. Greiner, S. Oestreich, S. Forster, and M. Antonietti, J. Am. Chem. Soc., 1997, 119, 10116.
A. Leyva, H. Garcia, and A. Corma, Tetrahedron, 2007, 63, 7097.
T. Y. Zhang and M. J. Allen, Tetrahedron Lett., 1999, 40, 5813.
J.W. Kim, J. Kim, D. H. Lee, and Y. Lee, Tetrahedron Lett., 2006, 47, 4745.
R. Srivastava, N. Venkatathri, D. Srinivas, P. Ratnasamy, Tetrahedron Lett., 2003, 44, 3649.
K. Hamza, R. Abu-Reziq, D. Avnir, and J. Blum, Organic Lett., 2004, 6, 925.
C. P. Mehnert, D. W. Weaver, and J. Y. Ying, J. Am. Chem. Soc., 1998, 120, 12289.
B. M. Bahanage, S.-I. Fujita, and M. Arai, J. Organomet. Chem., 2003, 687, 211.
J. Gil-Molto, S. Karlstrom, and C. Najera, Tetrahedron, 2005, 61, 12168.
G. Polotskaya, M. Goikhman, I. Podeshvo, V. Kudryavtsev, Z. Pientka, L. Brozova, and M. Bleha, Polymer, 2005, 46, 3730.
T. V. Magdesieva, A. V. Dolganov, A. V. Yakimansky, M. Ya. Goikhman, I. V. Podeshvo, and V. V. Kudryavtsev, Elektrokhimiya, 2007, 43, 1194 [Russ. J. Electrocthem. (Engl. Transl.), 2007, 43].
T. V. Magdesieva, A. V. Dolganov, A. V. Yakimansky, M. Ya. Goikhman, I. V. Podeshvo, and V. V. Kudryavtsev, Electrochim. Acta, 2008, 53, 3960.
T. V. Magdesieva, A. V. Dolganov, A. V. Yakimansky, M. Ya. Goikhman, and I. V. Podeshvo, Electrochim. Acta, 2009.
K. Winkler, A. De Bettencourt-Dias, and A. L. Balch, Chem. Mater., 2000, 12, 1386.
A. L. Balch, D. A. Costa, and K. Winkler, J. Am. Chem. Soc., 1998, 120, 9614.
S. S. Kamath, V. Uma, and T. S. Srivastava, Inorg. Chim. Acta, 1989, 161, 49.
D. E. McKenzie, Coord. Chem. Rev., 1971, 6, 187.
Y. Muranishi, Y. Wang, M. Odoko, and N. Okabe, Acta Crystallogr., 2005, C61, m307–m310.
C. M. Harris, H. R. H. Patil, and E. Sinn, Inorg. Chem., 1967, 6, 1102.
K. Sugiyama and K. Aoki, J. Electroanal. Chem., 1989, 262, 211.
G. Lu, R. Franze, Q. Zhang, and Y. Xu, Tetrahedron Lett., 2005, 46, 4255.
N. A. Bumagin and V. V. Bykov, Tetrahedron, 1997, 53, 14437.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1382–1389, July, 2009.
Rights and permissions
About this article
Cite this article
Magdesieva, T.V., Nikitin, O.M., Abdullin, R.M. et al. Electrochemical synthesis of PdII polynuclear complexes based on biquinolyl-containing polymers and their catalytic activity in the Suzuki reaction. Russ Chem Bull 58, 1423–1430 (2009). https://doi.org/10.1007/s11172-009-0190-4
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-009-0190-4