Sc(OTf)3-mediated silylation of hydroxy functional groups on a solid surface: A catalytic grafting method operating at room temperature

Angewandte Chemie - International Edition

Volumn 47, Issue 1, 2008, Pages 109-112

  Yeon, Ye Rim ^a   Park, Young Jun ^a   Lee, Ji Sung ^a   Park, Jung Woo ^a   Kang, Sin Gun ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

Glasses; Methallylsilane; Scandium; Silicon; Surface chemistry

Indexed keywords

CATALYTIC GRAFTING; METHALLYLSILANE; ROOM TEMPERATURE;

CATALYST ACTIVITY; CHEMICAL STABILITY; GLASS; GRAFTING (CHEMICAL); OXIDES; SCANDIUM; SILICON; SURFACE CHEMISTRY;

FUNCTIONAL GROUPS;

GLASS; MESYLIC ACID DERIVATIVE; SCANDIUM; SCANDIUM TRIFLATE; SILANE DERIVATIVE; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SURFACE PROPERTY; TEMPERATURE;

CATALYSIS; GLASS; MESYLATES; MOLECULAR STRUCTURE; SCANDIUM; SILANES; SILICON DIOXIDE; SURFACE PROPERTIES; TEMPERATURE;

EID: 37549012945     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703112     Document Type: Article

References (34)

1. a) K. B. Yoon, Acc. Chem. Res. 2007, 40, 29, and references therein;
2. b) F. Hoffmann, M. Cornelius, J. Morell, M. Fröba, Angew. Chem. 2006, 118, 3290;
3. Angew. Chem. Int. Ed. 2006, 45, 3216;
4. c) A. B. Descalzo, R. Martínez-Máñez, F. Sancenó, K. Hoffmann, K. Rurack, Angew. Chem. 2006, 118, 6068;
5. Angew. Chem. Int. Ed. 2006, 45, 5924;
6. d) G. J. A. A. Soler-Illia, P. Innocenzi, Chem. Eur. J. 2006, 12, 4478;
7. e) I. Slowing, B. G. Trewyn, V. S. Y. Lin, J. Am. Chem. Soc. 2006, 128, 14792;
8. f) A. Corma, H. Garcia, Adv. Synth. Catal. 2006, 348, 1391;
9. g) C. M. Crudden, M. Sateesh, R. Lewis, J. Am. Chem. Soc. 2005, 127, 10045;
10. h) E. J. Acosta, C. S. Carr, E. E. Simanek, D. F. Shantz, Adv. Mater. 2004, 16, 985;
11. i) Y. Fujimoto, A. Shimojima, K. Kuroda, Chem. Mater. 2003, 15, 4768;
12. j) P. Judeinstein, C. Sanchez, J. Mater. Chem. 1996, 6, 511.
13. Special issues on functional hybrid materials: a) J. Mater. Chem. 2005, 15, 3541;
14. b) Chem. Mater. 2001, 13, 3059.
15. E. F. Vansant, P. Van Der Voort, C. Vrancken in Studies in Surface Science and Catalysis, Vol. 93, Part II (Eds.: B. Delmon, T. Yates), Elsevier, Amsterdam, 1995.
16. a) S. Krämer, R. R. Fuierer, C. B. Gorman, Chem. Rev. 2003, 103, 4367;
17. b) D. S. Ginger, H. Zhang, C. A. Mirkin, Angew. Chem. 2004, 116, 30;
18. Angew. Chem. Int. Ed. 2004, 43, 30.
19. a) A. Ivanisevic, C. A. Mirkin, J. Am. Chem. Soc. 2001, 123, 7887;
20. b) H. Jung, R. Kulkarni, C. P. Collier, J. Am. Chem. Soc. 2003, 125, 12096;
21. c) D. J. Pena, M. P. Raphael, J. M. Byers, Langmuir 2003, 19, 9028.
22. T. Shimada, K. Aoki, Y. Shinoda, T. Nakamura, N. Tokunaga, S. Inagaki, T. Hayashi, J. Am. Chem. Soc. 2003, 125, 4688.
23. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999.
24. J.-W. Park, H.-J. Chang, C.-H. Jun, Synlett 2006, 771.
25. a) T. Suzuki, T. Watahiki, T. Oriyama, Tetrahedron Lett. 2000, 41, 8903;
26. b) T. Morita, Y. Okamoto, H. Sakurai, Tetrahedron Lett. 1980, 21, 835;
27. c) G. A. Olah, A. Husain, B. G. B. Gupta, G. F. Salem, S. C. Narang, J. Org. Chem. 1981, 46, 5212;
28. d) A. Hosomi, H. Sakurai, Chem. Lett. 1981, 85;
29. e) G. A. Olah, A. Husain, B. P. Singh, Synthesis 1983, 892.
30. For experimental procedures, see the Supporting Information.
31. The loading rates were determined by simultaneous elemental analysis of carbon and nitrogen.
32. -1 even after heating in toluene to reflux for 24 hours.
33. 1H NMR experiments, see the Supporting Information, Scheme S2.
34. Such trends were also observed by the XPS measurements on each sample of 4o and DABS-functionalized glasses (Supporting Information, Figure S3). The loading on ITO surface was evaluated by integrating the CV curve after subtracting non-Faradaic current.