Nanocrystalline magnesium oxide stabilized palladium(0): An efficient reusable catalyst for room temperature selective aerobic oxidation of alcohols

Advanced Synthesis and Catalysis

Volumn 353, Issue 4, 2011, Pages 606-616

  Layek, Keya ^a   Maheswaran, H ^a   Arundhathi, R ^a   Kantam, M Lakshmi ^a   Bhargava, Suresh K ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b RMIT UNIVERSITY   (Australia)

Author keywords

Aerobic oxidation; Alcohols; Aldehydes; Catalyst recycling; Heterogeneous catalysis

Indexed keywords

EID: 79952560253     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000591     Document Type: Article

References (83)

1. a) R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidation of Organic Compounds, Academic Press, New York, 1981;
2. b) M. Hudlicky, Oxidations in Organic Chemistry, American Chemical Society, Washington, DC., 1990.
3. R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catal. Today 2000, 57, 157.
4. a) D. Choudhary, S. Paul, R. Gupta, J. H. Clark, Green Chem.2006, 8, 479, and the references cited therein.
5. For discussions on traditional oxidation methods, also refer to: b) M. Hudlicky, in: Oxidations in Organic Chemistry, ACS Monograph Series, American Chemistry Society: Washington DC, 1990, p174;
6. c) M. B. Smith, in: Organic Synthesis, McGraw-Hill, Singapore, 1994, p 221;
7. nd edn., Wiley-VCH, New York, 1999, p 2583;
8. th edn., Wiley-Interscience, New York, 2007.
9. For a discussion of atom economy in organic synthesis see: a) B. M. Trost, Science 1991, 254, 1471;
10. b) B. M. Trost, Angew. Chem. 1995, 107, 285;
11. Angew. Chem. Int. Ed. Engl. 1995, 34, 259.
12. For references on homogeneous palladium catalysts for aerobic oxidation of alcohols see: a) K. Kaneda, Y. Fujii, K. Morioka, J. Org. Chem. 1996, 61, 4502;
13. b) K. Kaneda, Y. Fujii, K. Ebitani, Tetahedron Lett. 1997, 38, 9023;
14. c) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185;
15. d) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, Tetahedron Lett. 1998, 39, 6011;
16. e) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 6750;
17. f) G. Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636;
18. g) K. Hallman, C. Moberg, Adv. Synth. Catal. 2001, 343, 260;
19. h) M. J. Schultz, C. C. Park, M. S. Sigman, Chem. Commun. 2002, 3034;
20. i) D. R. Jensen, M. J. Schultz, J. A. Mueller, M. S. Sigman, Angew. Chem. 2003, 115, 3940;
21. Angew. Chem. Int. Ed. 2003, 42, 3810;
22. j) G. Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355;
23. k) T. Nishimura, S. Uemura, Synlett 2004, 201;
24. l) S. Paavola, K. Zetterberg, T. Privalov, I. Csoregh, C. Moberg, Adv. Synth. Catal. 2004, 346, 237;
25. m) T. Iwasawa, M. Tokunaga, Y. Obora, Y. Tsuji, J. Am. Chem. Soc. 2004, 126, 6554;
26. n) M. J. Schultz, S. S. Hamilton, D. R. Jensen, M. S. Sigman, J. Org. Chem. 2005, 70, 3343.
27. For references on heterogeneous palladium catalysts for aerobic oxidation of alcohols, see: o) T. Nishimura, N. Kakiuchi, M. Inoue, S. Uemura, Chem. Commun. 2000, 1245;
28. p) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620;
29. q) K. Moroi, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2002, 124, 11572;
30. r) D. R. Jensen, M. J. Schutz, J. A. Mueller, M. S. Sigman, Angew. Chem. 2003, 115, 3940;
31. Angew. Chem. Int. Ed. 2003, 42, 3810;
32. s) K. Mori, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2004, 126, 10657;
33. t) M. S. Kwon, N. Kim, C. M. Park, J. S. Lee, K. Y. Kang, J. Park, Org. Lett. 2005, 7, 1077;
34. u) U. R. Pillai, E. Sahle-Demessie, Green Chem. 2004, 6, 161;
35. v) B. Karimi, A. Zamani, J. H. Clark, Organometallics 2005, 24, 4695.
36. M. J. Schultz, C. C. Park, M. S. Sigman, Chem. Commun. 2002, 3034.
37. a) H. Yang, X. Han, Z. Ma, R. Wang, J. Liu, X. Ji, Green Chem. 2010, 12, 441;
38. b) T. Hara, M. Ishikawa, J. Sawada, N. Ichikuni, S. Shimazu, Green Chem. 2009, 11, 2034;
39. c) B. Karimi, A. Zamani, S. Abedi, J. H. Clark, Green Chem. 2009, 11, 109;
40. d) S. F. J. Hackett, R. M. Brydson, M. H. Gass, I. Harvey, A. D. Newman K. Wilson, A. F. Lee, Angew. Chem. 2007, 119, 8747;
41. Angew. Chem. Int. Ed. 2007, 46, 8593;
42. e) D. Choudhary, S. Paul, R. Gupta, J. H. Clark, Green Chem. 2006, 8, 479-482;
43. f) H. Wu, Q. Zhang, Y. Wang, Adv. Synth. Catal. 2005, 347, 1356;
44. g) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620;
45. h) M. Hayashi, K. Yamada, S. Nakayama, H. Hayashi, S. Yamazaki, Green Chem. 2000, 2, 257;
46. i) T. Nishimura, N. Kakiuchi, M. Inoue, S. Uemura, Chem. Commun. 2000, 1245.
47. G. Ann, H. Ahn, K. A. De Castro, H. Rhee, Synthesis 2010, 477.
48. a) J. Chen, Q. Zhang, Y. Wang, H. Wan, Adv. Synth. Catal. 2008, 350, 453;
49. b) U. R. Pillai, E. Sahle-Demessie, Green Chem. 2004, 6, 161;
50. c) F. Li, Q. Zhang, Y. Wang, Appl. Catal. A: Gen. 2008, 334, 217;
51. d) H. Wu, Q. Zhang, Y. Wang, Adv. Synth. Catal. 2005, 347, 1356;
52. e) Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204;
53. Angew. Chem. Int. Ed. 2003, 42, 194;
54. f) M. S. Kwon, N. Kim, C. M. Park, J. S. Lee, K. Y. Kang, J. Park, Org. Lett. 2005, 7, 1077.
55. a) M. L. Kantam, S. Roy, M. Roy, B. Sreedhar, B. M. Choudary, Adv. Synth. Catal. 2005, 347, 2002;
56. b) M. L. Kantam, S. Roy, M. Roy, M. S. Subhas, P. R. Likhar, B. Sreedhar, B. M. Choudary, Synlett 2006, 2747;
57. c) M. L. Kantam, R. Chakravarti, U. Pal, B. Sreedhar, S. Bhargava, Adv. Synth. Catal. 2008, 350, 822;
58. d) M. L. Kantam, R. Chakravarti, C. V. Reddy, B. Sreedhar, S. Bhargava, Adv. Synth. Catal. 2008, 350, 2544.
59. a) P. Jeevanandam, K. J. Klabunde, Langmuir 2002, 18, 5309;
60. b) K. J. Klabunde, R. Mulukutla, Nanoscale Materials in Chemistry, Wiley Interscience, New York, 2001, Chapter 7, p 23.
61. For various reactions catalyzed by NAP-MgO see: a) M. L. Kantam, U. Pal, B. Sreedhar, B. M. Choudary, Adv. Synth. Catal. 2007, 349, 1671;
62. b) M. L. Kantam, K. V. S. Ranganath, K. Mahendar, L. Chakrapani, B. M. Choudary, Tetrahedron Lett. 2007, 48, 7646;
63. c) B. M. Choudary, M. L. Kantam, K. V. S. Ranganath, K. Mahendar, B. Sreedhar, J. Am. Chem. Soc. 2004, 126, 3396;
64. d) B. M. Choudary, K. V. S. Ranganath, U. Pal, M. L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2005, 127, 13167;
65. e) M. L. Kantam, K. Mahender, S. Bhargava, J. Chem. Sci. 2010, 122, 63;
66. f) M. L. Kantam, L. Chakrapani, B. M. Choudary, Synlett 2008, 1946.
67. M. L. Kantam, S. Roy, M. Roy, B. Sreedhar, B. M. Choudary, Adv. Synth. Catal. 2005, 347, 2002.
68. H. P. Choo, K. Y. Liew, H. Liu, J. Mater. Chem. 2002, 12, 934.
69. a) K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani, K, Kaneda, J. Am. Chem. Soc. 2002, 124, 11572;
70. b) M. L. Kantam, K. B. S. Kumar, P. Srinivas, B. Sreedhar, Adv. Synth. Catal. 2007, 349, 1141;
71. c) A. Cwik, Z. Hell, F. Figueras, Adv. Synth. Catal. 2006, 348, 523.
72. For mechanistic investigations on various types of Pd-catalyzed aerobic alcohol oxidation, see: a) B. A. Steinhoff, S. R. Fix, S. S. Stahl, J. Am. Chem. Soc. 2002, 124, 766;
73. b) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202;
74. c) J. Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355;
75. d) J. Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui, R. A. Sheldon, Adv. Synth. Catal. 2003, 345, 497;
76. e) J. A. Mueller, M. S. Sigman, J. Am. Chem. Soc. 2003, 125, 7005;
77. f) R. M. Trend, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 4482;
78. g) R. J. Nielsen, J. M. Keith, B. M. Stoltz, W. A. Goddard, J. Am. Chem. Soc. 2004, 126, 7967;
79. h) J. A. Mueller, C. P. Goller, M. S. Sigman, J. Am. Chem. Soc. 2004, 126, 9724;
80. i) M. M. Konnick, I .A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 10212;
81. j) T. Privalov, C. Linde, Z. Zetterberg, C. Moberg, Organometallics 2004, 24, 885;
82. k) M. J. Schultz, R. S. Adler, W. Zierkiewicz, T. Privalov M. S. Sigman, J. Am. Chem. Soc. 2005, 127, 8499;
83. l) B. A. Steinhoff, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 11268.