Synthesis of Triscatechol Derivatives - Building Blocks with an Idealized C₃-Symmetry for Metallo-Supramolecular Chemistry

Abstract

A series of triscatechols with an idealized axis of C₃-symmetry were synthesized. Hereby amide, imine or direct bonds are introduced as linkage between the catechol units and various C₃-symmetric backbones.

Key words

Pd-coupling - amide - imine - catechol - ligand

References

• 1 Schalley CA. Lützen A. Albrecht M. Chem.-Eur. J.  2004,  10:  1072 
• 2a Saalfrank RW. Bernt I. Curr. Opin. Solid State Mater. Sci.  1998,  3:  407 
• 2b Lehn J.-M. Supramolecular Chemistry - Concepts and Perspectives   VCH; Weinheim: 1995. 
• 2c Caulder D. Raymond KN. J. Chem. Soc., Dalton Trans.  1999,  1185 
• 2d Olenyuk B. Fechtenkötter A. Stang PJ. J. Chem. Soc., Dalton Trans.  1998,  1707 
• 3 Albrecht M. Janser I. Meyer S. Weis P. Fröhlich R. Chem. Commun.  2003,  2854 
• 5 Albrecht M. Janser I. Kamptmann S. Weis P. Wibbeling B. Fröhlich R. Dalton Trans.  2004,  37 
• 6 Karpishin TB. Stack TDP. Raymond KN. J. Am. Chem. Soc.  1993,  115:  6115 
• 7 Albrecht M. Angew. Chem. Int. Ed.  1999,  38:  3463 ; Angew. Chem. 1999, 111, 3671
• 8a Brückner C. Powers RE. Raymond KN. Angew. Chem. Int. Ed.  1998,  37:  1837 ; Angew. Chem. 1998, 110, 1937
• 8b Caulder D. Brückner C. Powers RE. König S. Parac TN. Leary JA. Raymond KN. J. Am. Chem. Soc.  2001,  123:  8923 
• 9a Li P. Xu J.-C. Chin. J. Chem.  2000,  18:  456 ; Chem. Abstr. 2000, 133, 252669
• 9b Li P. Xu J.-C. Tetrahedron  2000,  56:  9949 
• 9c Speicher A. Klaus T. Eicher T. J. Prakt. Chem.  1998,  340:  581 
• 10 McOmie JFW. West DE. Org. Synth. Collect. Vol. V   Wiley; New York: 1973.  p.412 
• 11a Aguiari A. Bullita E. Casellato U. Guerriero P. Tamburini S. Vigato PA. Inorg. Chim. Acta  1992,  202:  157 
• 11b Guerriero P. Tamburini S. Vigato PA. Coord. Chem. Rev.  1995,  139:  17 
• 12 Deeming AJ. Hogarth G. Lee M.-Y. Saha M. Redmond SP. Phetmung H. Orpen AG. Inorg. Chim. Acta  2000,  309:  109 
• 13 Pizzala H. Carles M. Stone WEE. Thevand A. J. Chem. Soc., Perkin Trans. 2  2000,  935 
• 14 Prevot-Halter I. Smith TJ. Weiss J. J. Org. Chem.  1997,  62:  2816 
• 15 Albrecht M. Schneider M. Synthesis  2000,  1557 
• 16 Temme O. Dickner T. Laschat S. Fröhlich R. Kotila S. Bergander K. Eur. J. Org. Chem.  1998,  651 
• 17 Otwinowski Z. Minor W. Methods in Enzymology  1997,  276:  307 
• 18 Sheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr.  1990,  A46:  467 

4

Albrecht, M.; Janser, I.; Runsink, J.; Raabe, G.; Fröhlich, R. 2004, submitted for publication.

19

Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-232929. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, CambridgeCB2 1EZ, UK [fax: [phone], e-mail: [e-mail]].