Chemoselective oxidation of secondary alcohols using a ruthenium phenylindenyl complex

Organometallics

Volumn 32, Issue 2, 2013, Pages 660-664

  Manzini, Simone ^a   Urbina Blanco, César A ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL OXIDATION; CHEMO-SELECTIVITY; CHEMOSELECTIVE OXIDATION; COCATALYST; COMPLEX 1; SECONDARY ALCOHOLS;

ACETONE; CATALYTIC OXIDATION; RUTHENIUM;

RUTHENIUM COMPOUNDS;

EID: 84872969515     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om301156v     Document Type: Article

References (47)

1. March, J. and Smith, M. B., March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6 th ed.; Wiley: Hoboken, NJ, 2007.
2. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156
3. Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39-45
4. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660
5. Li, J. J.; Corey, E. J. Oxidation. In Name Reactions for Functional Group Transformations; Wiley: Hoboken, NJ, 2010; pp 159-332.
6. Thorson, M. K.; Klinkel, K. L.; Wang, J.; Williams, T. J. Eur. J. Inorg. Chem. 2009, 2009, 295-302
7. Sheldon, R. A. Green Chemistry: Catalysis and Waste Minimization. In Methods and Reagents for Green Chemistry; Wiley: Hoboken, NJ, 2007; pp 189-199.
8. Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774-781
9. Sheldon, R. A. Chem. Soc. Rev. 2012, 41, 1437-1451
10. Larock, R. C. Comprehensive Organic Transformations; Wiley-VCH: New York, 1999.
11. Berini, C.; Winkelmann, O. H.; Otten, J.; Vicic, D. A.; Navarro, O. Chem. Eur. J. 2010, 16, 6857-6860
12. Prades, A.; Peris, E.; Albrecht, M. Organometallics 2011, 30, 1162-1167
13. Yi, C. S.; Zeczycki, T. N.; Guzei, I. A. Organometallics 2006, 25, 1047-1051
14. Adair, G. R. A.; Williams, J. M. J. Tetrahedron Lett. 2005, 46, 8233-8235
15. Putignano, E.; Bossi, G.; Rigo, P.; Baratta, W. Organometallics 2012, 31, 1133-1142
16. Moyer, S. A.; Funk, T. W. Tetrahedron Lett. 2010, 51, 5430-5433
17. Do, Y.; Ko, S.-B.; Hwang, I.-C.; Lee, K.-E.; Lee, S. W.; Park, J. Organometallics 2009, 28, 4624-4627
18. Wang, G.-Z.; Andreasson, U.; Backvall, J.-E. J. Chem. Soc. Chem. Commun. 1994, 1037-1038
19. Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc. Chem. Commun. 1991, 473-475
20. Buffin, B. P.; Clarkson, J. P.; Belitz, N. L.; Kundu, A.; Mol., J.; Catal, A. Chem 2005, 225, 111-116
21. Liu, L.; Yu, M.; Wayland, B. B.; Fu, X. Chem. Commun. 2010, 46, 6353-6355
22. Singh, P.; Singh, A. K. Organometallics 2010, 29, 6433-6442
23. Rout, L.; Nath, P.; Punniyamurthy, T. Adv. Synth. Catal. 2007, 349, 846-848
24. Singh, P.; Singh, A. K. Eur. J. Inorg. Chem. 2010, 2010, 4187-4195
25. Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 1977-1986
26. Sloboda-Rozner, D.; Alsters, P. L.; Neumann, R. J. Am. Chem. Soc. 2003, 125, 5280-5281
27. Tauchman, J.; Therrien, B.; Süss-Fink, G.; Ště pnička, P. Organometallics 2012, 31, 3985-3994
28. Shi, F.; Tse, M. K.; Beller, M. Chem. Asian J. 2007, 2, 411-415
29. Jacobson, S. E.; Muccigrosso, D. A.; Mares, F. J. Org. Chem. 1979, 44, 921-924
30. Landers, B.; Berini, C.; Wang, C.; Navarro, O. J. Org. Chem. 2011, 76, 1390-1397
31. Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. J. Org. Chem. 2003, 68, 1601-1602
32. Gabrielsson, A.; van Leeuwen, P.; Kaim, W. Chem. Commun. 2006, 4926-4927
33. Oppenauer, R. V. Recl. Trav. Chim. Pays-Bas 1937, 56, 137-144
34. Urbina-Blanco, C. A.; Manzini, S.; Gomes, J. P.; Doppiu, A.; Nolan, S. P. Chem. Commun. 2011, 47, 5022-5024
35. Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 6786-6801
36. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102
37. Bäckvall, J.-E. J. Organomet. Chem. 2002, 652, 105-111
38. Manzini, S.; Urbina-Blanco, C. A.; Poater, A.; Slawin, A. M. Z.; Cavallo, L.; Nolan, S. P. Angew. Chem., Int. Ed. 2012, 51, 1042-1045
39. Manzini, S.; Blanco, C. A. U.; Nolan, S. P. Adv. Synth. Catal. 2012, 354, 3036-3044
40. Almeida, M. L. S.; Kočovský, P.; Bäckvall, J.-E. J. Org. Chem. 1996, 61, 6587-6590.
41. Coleman, M. G.; Brown, A. N.; Bolton, B. A.; Guan, H. Adv. Synth. Catal. 2010, 352, 967-970
42. Krohn, K.; Knauer, B.; Küpke, J.; Seebach, D.; Beck, A. K.; Hayakawa, M. Synthesis 1996, 1996, 1341-1344
43. Almeida, M. L. S.; Beller, M.; Wang, G.-Z.; Bäckvall, J.-E. Chem. Eur. J 1996, 2, 1533-1536
44. Hanasaka, F.; Fujita, K.-i.; Yamaguchi, R. Organometallics 2004, 23, 1490-1492
45. Henderson, R. K.; Jimenez-Gonzalez, C.; Constable, D. J. C.; Alston, S. R.; Inglis, G. G. A.; Fisher, G.; Sherwood, J.; Binks, S. P.; Curzons, A. D. Green Chem. 2011, 13, 854-862
46. Conley, B. L.; Pennington-Boggio, M. K.; Boz, E.; Williams, T. J. Chem. Rev. 2010, 110, 2294-2312
47. Primary alcohols are challenging substrates for Oppenauer oxidations, due often to the disfavored equilibrium to the aldehyde species, as was well established by Oppenauer in the following review: Djerassi, C. In Organic Reactions; Wiley: Hoboken, NJ, 2004.