Copper-catalyzed tandem oxidation-olefination process

Organic Letters

Volumn 11, Issue 1, 2009, Pages 41-44

  Davi, Michaël ^a   Lebel, Hélène ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; COPPER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; ALKENES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 59649112592     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802299d     Document Type: Article

References (80)

1. For recent selected examples, see: (a) Donohoe, T. J.; Harris, R. M.; Burrows, J.; Parker, J. J. Am. Chem. Soc. 2006, 128, 13704-13705.
2. (b) Wang, Y.-G.; Takeyama, R.; Kobayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 3320-3323.
3. (c) Young, I. S.; Kerr, M. A. J. Am. Chem. Soc. 2007, 129, 1465-1469.
4. (d) Yang, H.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2008, 130, 9238-9239.
5. (e) Selig, P.; Bach, T. Angew. Chem. Int. Ed. 2008, 47, 5082-5084.
6. Swern: (a) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198-2200. DMP:
7. 4:
8. 2:
9. (d) Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815-3818.
10. (e) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337-1338.
11. (f) Blackburn, L.; Pei, C.; Taylor, R. Synlett 2002, 215-218.
12. (g) Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem. Res. 2005, 38, 851-869. IBX:
13. (h) Crich, D.; Mo, X.-S. Synlett., 1999, 67-68.
14. (i) Maiti, A.; Yadav, J. S. Syntth. Commun. 2001, 31, 1499-1506. TPAP/NMO:
15. (j) MacCoss, R. N.; Balskus, E. P.; Ley, S. V. Tetrahedron Lett. 2003, 44, 7779-7781. PCC:
16. 3-pyridine:
17. (l) Crisostomo, F. R. P.; Carrillo, R.; Martin, T.; Garcia-Tellado, F.; Martin, V. S. J. Org. Chem. 2005, 70, 10099-10101. TEMPO/BAIB:
18. (m) Vatèle, J.-M. Tetrahedron Lett. 2006, 47, 715-718.
19. For recent and selected applications of these tandem processes in total synthesis, see:
20. (a) Shet, J.; Desai, V.; Tilve, S. Synthesis 2004, 1859-1863.
21. (b) Yadav, J. S.; Reddy, M. S.; Rao, P. P.; Prasad, A. R. Synthesis 2006, 4005-4012.
22. (c) Goksel, H.; Stark, C. B. W. Org. Lett. 2006, 8, 3433-3436.
23. (d) Ichikawa, Y.; Yamaoka, T.; Nakano, K.; Kotsuki, H. Org. Lett. 2007, 9, 2989-2992.
24. (e) Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Chem.-Eur. J. 2007, 13, 5515-5538.
25. (f) Yadav, J. S.; Reddy, P. M. K.; Reddy, P. V. Tetrahedron Lett. 2007, 48, 1037-1039.
26. (g) Majik, M.; Shet, J.; Tilve, S.; Parameswaran, P. S. Synthesis 2007, 663-665.
27. (h) Reddy, J. S.; Rao, B. V. J. Org. Chem. 2007, 72, 2224-2227.
28. (i) Yadav, J. S.; Kumar, N. N.; Prasad, A. R. Synthesis 2007, 1175-1178.
29. (j) Pandya, B. A.; Snapper, M. L. J. Org. Chem. 2008, 73, 3754-3758.
30. (a) Lebel, H.; Paquet, V.; Proulx, C. Angew. Chem., Int. Ed. 2001, 40, 2887-2890.
31. (b) Grasa, G. A.; Moore, Z.; Martin, K. L.; Stevens, E. D.; Nolan, S. P.; Paquet, V.; Lebel, H. J. Organomet. Chem. 2002, 658, 126-131.
32. (c) Lebel, H.; Paquet, V. Org. Lett. 2002, 4, 1671-1674.
33. (d) Lebel, H.; Guay, D.; Paquet, V.; Huard, K. Org. Lett. 2004, 6, 3047-3050.
34. (e) Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 320-328.
35. (f) Paquet, V.; Lebel, H. Synthesis 2005, 1901-1905.
36. Lebel, H.; Ladjel, C. Organomet al.lics 2008, 27, 2676-2678.
37. (a) Lebel, H.; Davi, M.; Diez-Gonzalez, S.; Nolan, S. P. J. Org. Chem. 2007, 72, 144-149.
38. (b) Lebel, H.; Davi, M.; Stoklosa, G. T. J. Org. Chem. 2008, 73, 6828-6830.
39. (c) Lebel, H.; Davi, M. AdV. Synth. Catal. 2008, 350, 2352-2358.
40. For recent examples of application in total synthesis, see: (a) Nagashima, H.; Gondo, M.; Masuda, S.; Kondo, H.; Yamaguchi, Y.; Matsubara, K. Chem. Commun. 2003, 442-443.
41. (b) Kwon, M. S.; Woo, S. K.; Na, S. W.; Lee, E. Angew. Chem., Int. Ed. 2008, 47, 1733-1735.
42. (c) Zhang, H.; Reddy, M. S.; Phoenix, S.; Deslongchamps, P. Angew. Chem., Int. Ed. 2008, 47, 1272-1275.
43. (d) Lebel, H.; Parmentier, M. Org. Lett. 2007, 9, 3563-3566.
44. (a) Lebel, H.; Ladjel, C. J. Organomet. Chem. 2005, 690, 5198-5205.
45. (b) Lebel, H.; Ladjel, C. J. Org. Chem. 2005, 70, 10159-10161.
46. (c) Lebel, H.; Ladjel, C.; Brethous, L. J. Am. Chem. Soc. 2007, 129, 13321-13326.
47. (d) Davi, M.; Lebel, H. Chem. Commun. 2008, 4974-4976.
48. (a) Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810-3813.
49. (b) Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. J. Org. Chem. 2005, 70, 3343-3352.
50. (c) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229.
51. Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 11152-11153.
52. Kim and co-workers have reported a tandem oxidation-olefination process using a ruthenium-catalyzed aerobic oxidation and stoichiometric stabilized phosphorus ylides; see: Kim, G.; Lee, D. G.; Chang, S. Bull. Korean Chem. Soc. 2001, 22, 943-944.
53. For reviews, see: (a) Punniyamurthy, T.; Rout, L. Coord. Chem. Rev. 2008, 252, 134-154.
54. (b) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Gautier, A.; Dumeunier, R.; Dodo, K.; Philippart, F.; Chelle-Regnault, I.; Mutonkole, J.-L.; Brown, S. M.; Urch, C. J. Aerobic, met al.-catalyzed oxidation of alcohols, Transition Met al.s for Organic Synthesis; Wiley-VCH: Wemheim, 2004; Vol. 2, pp 437-478.
55. (c) Schultz, M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227-8241.
56. Markó, I. E.; Gautier, A.; Dumeunier, R.; Doda, K.; Philippart, F.; Brown, S. M.; Urch, C. J. Angew. Chem., Int. Ed. 2004, 43, 1588-1591.
57. For earlier work by Markó, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044-2046.
58. (b) Markó, I. E.; Gautier, A.; Chelle-Regnaut, I.; Giles, P. R.; Tsukazaki, M.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1998, 63, 7576-7577.
59. (c) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.; Gautier, A.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999, 64, 2433-2439.
60. (d) Markó, I. E.; Gautier, A.; Mutonkole, J. L.; Dumeunier, R.; Ates, A.; Urch, C. J.; Brown, S. M. J. Organomet. Chem. 2001, 624, 344-347.
61. (e) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.; Gautier, A.; Dumeunier, R.; Philippart, F.; Doda, K.; Mutonkole, J.-L.; Brown, S. M.; Urch, C. J. Adv. Inorg. Chem. 2004, 56, 211-240.
62. Another catalytic system using copper in combination with TEMPO derivatives has been developed. Nevertheless, due to the sterically hindered environnement at the copper center, the secondary alcohols are slowly oxidated. See: (a) Gamez, P.; Arends, I. W. C. E.; Reedijk, J.; Sheldon, R. A. Chem. Commun. 2003, 2414-2415.
63. (b) Gamez, P.; Arends, I. W. C. E.; Sheldon, R. A.; Reedijk, J. AdV. Synth. Catal. 2004, 346, 805-811.
64. (c) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509.
65. (d) Gamez, P.; Arends, I. W. C. E.; Sheldon, R. A.; Reedijk, J. Adv. Synth. Catal. 2004, 346, 805-811.
66. (e) Jiang, N.; Ragauskas, A. J. Org Lett. 2005, 7, 3689-3692.
67. (f) Jiang, N.; Ragauskas, A. J. J. Org. Chem. 2006, 71, 7087-7090.
68. (g) Velusamy, S.; Srinivasan, A.; Punniyamurthy, T. Tetrahedror Lett. 2006, 47, 923-926.
69. (h) Striegler, S. Tetrahedron 2006, 62, 9109-9114.
70. (i) Mannam, S.; Alamsetti, S. K.; Sekar, G. Adv. Synth. Catal. 2007, 349, 2253-2258.
71. (j) Shen, H.-Y.; Ying, L.-Y.; Jiang, H, -L.; Judeh, Z. M. A. Int. J. Mol. Sci. 2007, 8, 505-512.
72. 1H NMR, or TLC analysis. The solvent was removed under reduced pressure, and the crude alkene was purified by flash chromatography on silica gel.
73. 2 is required, as this reagent is destroyed over time in the reaction mixture.
74. In the palladium-catalyzed aerobic oxidation, only moderate conversions were observed for the allylic alcohols
75. (see ref 11). For modified conditions for the palladium-catalyzed aerobic oxidation of allylic alcohols, see: Batt, F.; Bourcet, E.; Kassab, Y.; Fache, F. Synlett., 2007, 1869-1872.
76. In some cases, racemization was observed during the palladiumcatalyzed aerobic oxidation, see ref 11.
77. For examples of Brönsted acid-catalyzed Wittig reaction, see: (a) Rüchardt, C.; Eichler, S.; Panse, P. Angew. Chem., Int. Ed. 1963, 2, 619.
78. (b) Bose, A. K.; Manhas, M. S.; Ramer, R. M. J. Chem. Soc. C. 1969, 2728-2730.
79. (c) Patil, V. J.; Mävers, U. Tetrahedron Lett. 1996, 67, 1281-1284.
80. (d) Barrett, A. G. M.; Hamprecht, D.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 8608-8615.