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Additional info for Comprehensive Coordination Chemistry II, Volume 1: Fundamentals: Ligands, Complexes, Synthesis, Purification, and Structure

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This method of lithiating either one or both of the methyl groups of 4,40 -, 5,50 -, or 6,60 -dimethyl-bpy and then quenching the anionic species with an electrophile has been exploited in the synthesis of many substituted symmetric and unsymmetric bipyridine derivatives. 83 Bipyridines with aryl substituents have been prepared in high yield by Suzuki coupling methods. 84 R1 Br R2 N + R1 N Br R3 B(OH)2 Pd(PPh3)4 toluene Na2CO3 H2O,MeOH R2 N R3 N R1 R3 (16) R1 = CH3, R2 = R3 = H (17) R1 = R3 = H, R2 = CH3 (18) R1 = R2 = R3 = CH3 R2 Scheme 9 Intramolecular charge transfer has been observed in bipyridine ligands bearing electron-donating groups (the bipyridine rings serve as the electron acceptor) such as pyrenyl.

Heterocyclic Nitrogen-donor Ligands. , Gillard, R. , McCleverty, J. A. ; Pergamon Press: Oxford, 1987; Vol. 2. 14. Burstall, F. H. J. Chem. Soc. 1938, 1662–1672. 15. Case, F. ; Kasper, T. J. J. Am. Chem. Soc. 1956, 78, 5842–5844. 16. MacBride, J. A. ; Wright, P. ; Wakefield, B. J. Tetrahedron Lett. 1981, 22, 4545–4548. 17. Sasse, W. H. F. Org. Synth. 1966, 46, 5–10. 18. Badger, G. ; Sasse, W. H. F. Adv. Heterocycl. Chem. 1963, 2, 179–202. 19. Kro¨hnke, F. Synthesis 1976, 1–24. 20. ; Benneche, T.

Tetrahedron Lett. 2001, 42, 7787–7790. Savage, S. ; Smith, A. ; Fraser, C. L. J. Org. Chem. 1998, 63, 10048–10051. Smith, A. ; Savage, S. ; Love, J. ; Fraser, C. L. Org. Synth. 2001, 78, 51–62. ; Foxman, B. ; Lin, W. Inorg. Chim. Acta 1999, 288, 215–219. Siegel, J. ; Loren, J. C. Angew. , Int. Ed. Engl. 2001, 40, 754–757. ; Terashima, M. Synthesis 1984, 936–938. Fernando, S. R. ; Maharoof, U. S. ; Deshayes, K. ; Kinstle, T.

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