Transformation of Silanes into Silanols using Water and Recyclable Metal Nanoparticle Catalysts

ChemCatChem

Volumn 4, Issue 4, 2012, Pages 521-524

  Jeon, Mina ^a   Han, Junghoon ^a   Park, Jaiwook ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Green chemistry; Heterogeneous catalysis; Oxidation; Palladium; Silanes

Indexed keywords

ALKYNYLS; AMBIENT CONDITIONS; GOLD CATALYSTS; GREEN CHEMISTRY; HYDROGENATION REACTIONS; ORGANOSILANES; OXYGEN ATMOSPHERE; OXYHYDROXIDES; PALLADIUM CATALYST; SIDE PRODUCTS; SILANOLS;

CATALYSIS; GOLD; HYDROGENATION; METAL NANOPARTICLES; OXIDATION; PALLADIUM; RHODIUM; SILANES;

CATALYSTS;

EID: 84859136224     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100456     Document Type: Article

References (57)

1. R. Zhang, J. E. Mark, A. Pinhas, Macromolecules 2000, 33, 3508-3510;
2. V. Chandrasekhar, R. Boomishankar, S. Nagendran, Chem. Rev. 2004, 104, 5847-5910;
3. R. Murugavel, M. G. Walawalkar, M. Dan, H. W. Roesky, C. N. R. Rao, Acc. Chem. Res. 2004, 37, 763-774;
4. Q. Zhou, S. Yan, C. C. Han, P. Xie, R. Zhang, Adv. Mater. 2008, 20, 2970-2976.
5. K. Hirabayashi, Y. Nishihara, A. Mori, T. Hiyama, Tetrahedron Lett. 1998, 39, 7893-7896;
6. K. Hirabayashi, J. Kawashima, Y. Nishihara, A. Mori, T. Hiyama, Org. Lett. 1999, 1, 299-302;
7. K. Hirabayashi, A. Mori, J. Kawashima, M. Suguro, Y. Nishihara, T. Hiyama, J. Org. Chem. 2000, 65, 5342-5349;
8. S. E. Denmark, M. H. Ober, Adv. Synth. Catal. 2004, 346, 1703-1714.
9. S. M. Sieburth, W. Mu, J. Org. Chem. 1993, 58, 7584-7586;
10. K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464.
11. W. Adam, R. Mello, R. Curci, Angew. Chem. 1990, 102, 916-917; Angew. Chem. Int. Ed. Engl. 1990, 29, 890-891;
12. J. A. Cella, J. C. Carpenter, J. Organomet. Chem. 1994, 480, 23-26.
13. Homogeneous catalysts with water:
14. M. Lee, S. Ko, S. Chang, J. Am. Chem. Soc. 2000, 122, 12011-12012;
15. Y. Lee, D. Seomoon, S. Kim, H. Han, S. Chang, P. H. Lee, J. Org. Chem. 2004, 69, 1741-1743;
16. E. A. Ison, R. A. Corbin, M. M. Abu-Omar, J. Am. Chem. Soc. 2005, 127, 11938-11939;
17. R. A. Corbin, E. A. Ison, M. M. Abu-Omar, Dalton Trans. 2009, 2850-2855.
18. Homogeneous catalysts with oxidants other than water:
19. E. Matarasso-Tchiroukhine, J. Chem. Soc. Chem. Commun. 1990, 681-682;
20. U. Schubert, C. Lorenz, Inorg. Chem. 1997, 36, 1258-1259;
21. K. Valliant-Saunders, E. Gunn, G. R. Shelton, D. A. Hrovat, W. T. Borden, J. M. Mayer, Inorg. Chem. 2007, 46, 5212-5219;
22. R. Ishimoto, K. Kamata, N. Mizuno, Angew. Chem. 2009, 121, 9062-9066; Angew. Chem. Int. Ed. 2009, 48, 8900-8904;
23. Y. Okada, M. Oba, A. Arai, K. Tanaka, K. Nishiyama, W. Ando, Inorg. Chem. 2010, 49, 383-385.
24. Heterogeneous catalysts with water:
25. K. Mori, M. Tano, T. Mizugaki, K. Ebitani, K. Kaneda, New J. Chem. 2002, 26, 1536-1538;
26. E. Choi, C. Lee, Y. Na, S. Chang, Org. Lett. 2002, 4, 2369-2371;
27. T. Mitsudome, S. Arita, H. Mori, T. Mizugaki, K. Jitsukawa, K. Kaneda, Angew. Chem. 2008, 120, 8056-8058; Angew. Chem. Int. Ed. 2008, 47, 7938-7940;
28. T. Mitsudome, A. Noujima, T. Mizugaki, K. Jitsukawa, K. Kaneda, Chem. Commun. 2009, 5302-5304;
29. B. P. S. Chauhan, A. Sarkar, M. Chauhan, A. Roka, Appl. Organomet. Chem. 2009, 23, 385-390;
30. N. Asao, Y. Ishikawa, N. Hatakeyama, Menggenbateer, Y. Yamamoto, M. Chen, W. Zhang, A. Inoue, Angew. Chem. 2010, 122, 10291-10293; Angew. Chem. Int. Ed. 2010, 49, 10093-10095;
31. J. John, E. Gravel, A. Hagège, H. Li, T. Gacoin, E. Doris, Angew. Chem. 2011, 123, 7675-7678; Angew. Chem. Int. Ed. 2011, 50, 7533-7536.
32. 2:
33. W. Adam, H. Garcia, C. M. Mitchell, C. R. Saha-Möller, O. Weichold, Chem. Commun. 1998, 2609;
34. W. Adam, A. Corma, H. García, O. Weichold, J. Catal. 2000, 196, 339-344;
35. W. Adam, C. R. Saha-Möller, O. Weichold, J. Org. Chem. 2000, 65, 2897-2899.
36. Pd/AlO(OH):
37. M. S. Kwon, N. Kim, C. M. Park, J. S. Lee, K. Y. Kang, J. Park, Org. Lett. 2005, 7, 1077-1709;
38. M. S. Kwon, N. Kim, S. H. Seo, I. S. Park, R. K. Cheedrala, J. Park, Angew. Chem. 2005, 117, 7073-7075; Angew. Chem. Int. Ed. 2005, 44, 6913-6915;
39. M. S. Kwon, I. S. Park, J. S. Jang, J. S. Lee, J. Park, Org. Lett. 2007, 9, 3417-3419;
40. M.-J. Kim, W.-H. Kim, K. Han, Y. K. Choi, J. Park, Org. Lett. 2007, 9, 1157-1159;
41. M. S. Kwon, S. Kim, S. Park, W. Bosco, R. K. Chidrala, J. Park, J. Org. Chem. 2009, 74, 2877-2879.
42. See Supporting Information.
43. Rh/AlO(OH):
44. I. S. Park, M. S. Kwon, N. Kim, J. S. Lee, K. Y. Kang, J. Park, Chem. Commun. 2005, 5667-5669;
45. I. S. Park, M. S. Kwon, K. Y. Kang, J. S. Lee, J. Park, Adv. Synth. Catal. 2007, 349, 2039-2047.
46. Au/AlO(OH): S. Kim, S. W. Bae, J. S. Lee, J. Park, Tetrahedron 2009, 65, 1461-1466.
47. Ru/AlO(OH):
48. W. H. Kim, I. S. Park, J. Park, Org. Lett. 2006, 8, 2543-2545;
49. S. Kim, M. S. Kwon, J. Park, Tetrahedron Lett. 2010, 51, 4573-4575;
50. E. Y. Lee, Y. Kim, J. S. Lee, J. Park, Eur. J. Org. Chem. 2009, 2943-2947.
51. Cu/AlO(OH):
52. I. S. Park, M. S. Kwon, Y. Kim, J. S. Lee, J. Park, Org. Lett. 2008, 10, 497-500;
53. S. Kim, D. Kim, J. Park, Adv. Synth. Catal. 2009, 351, 2573-2578;
54. E. Y. Lee, J. Park, ChemCatChem 2011, 3, 1127-1129.
55. Z. M. Michalska, Transition Met. Chem. 1980, 5, 125-129;
56. Y. Liu, I. Imae, A. Makishima, Y. Kawakami, Sci. Technol. Adv. Mater. 2003, 4, 27-34.
57. Some of the silane was consumed by reaction with water in the solvent or in the matrix to form the silanol.