Wacker- type oxidation of alkynes into 1, 2-diketones using molecular oxygen

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1841-1844

  Ren, Wei ^a   Xia, Yuanzhi ^a   Ji, Shun Jun ^a   Zhang, Yong ^a   Wan, Xiaobing ^a   Zhao, Jing ^b  

^a SOOCHOW UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; KETONE; OXYGEN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION;

ALKYNES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXYGEN;

EID: 65249159205     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900344g     Document Type: Article

References (55)

1. For recent reviews, see: (a) Tsuji. J. Pure Appl. Chem. 1999, 71, 1539-1547.
2. (b) Takacs, J. M.; Jiang, X. Curr. Org. Chem. 2003, 7, 369- 396.
3. (c) Cornell, C. N.; Stgman, M. S. Inorg. Chem. 2007, 46, 1903-1909.
4. (d) Kotov. V.; Scarborough, C. C; Stahl, S. S. Iorg. Chem. 2007, 46, 1910-1923.
5. For representative examples, see: (a) Báckvall, J.-E.; Åkermark, B.; Ljunggren, S, O.J. Chem. Soc, Chem. Commun. 1977, 264-265.
6. (b) Zaw, K.; Henry, P. M. J. Org. Chem. 1990, 55. 1842-1847.
7. (c) Nelson, D. J.: Li, R.; Brammer. C. J. Am. Chem. Soc. 2001, 123, 1564-1568.
8. (d) Keith, J. A.; Oxgaard, J.; Goddard, W. A., III. J. Am. Chem. Soc. 2006, 128, 3132- 3233.
9. (e) Keith. J. A.; Nielsen. R. J.; Oxgaard, J.; Goddard, W. A., Ill J. Am. Chem. Soc. 2007, 129, 12342-12343.
10. (f) Cornell. C. N.; Sigman, M. S. J. Am Chem. Soc. 2005, 127, 2796-2797.
11. (g) Havashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036-3037.
12. (3) For representative examples, see: (a) Hosokawa, T.; Uno, T.; Inui, S.; Murahashi, S.-I. J. Am. Chem. Soc. 1981, 103, 2318-2323.
13. (b) Uozumi. Y.: Kato. K.: Hayashi. T. J. Am. Chem. Soc. 1997, 119, 5063-5064.
14. (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Org. Chem. 1998, 63, 5071-5075.
15. (d) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625.
16. (e) Arai, M. A.; Kuraishi, M.; Arai. T.; Sasai. H. J. Am. Chem. Soc. 2001, 123. 2907-2908.
17. (f) Trend, R. M.; Ramtohul, Y. K.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892- 2895.
18. (g) Trend. R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778-17788.
19. (h) Wang, F.; Zhang. Y.; Yang, G.; Zhang, W. Ttrahedron Lett. 2007, 48, 4179-4182.
20. (a) ten Brink. G.-J.; Arends, I. W. C. E.; Papadogianakis, G.; Sheldon. R. A. Chem. Commun. 1998, 2359-2360.
21. (b) ten Brink, G.-J.; Arends, I. W. C. E.; Papadogianakis, G.; Sheldon, R. A. Appl. Catal., A 2000, 194-195, 435-442.
22. (c) Mũniz, K. Adv. Synth. Catal. 2004, 346, 1425- 1428.
23. (d) Mitsudome. T.; Umetani. T.; Nosaka. N.; Mori, K.; Mizugaki. T.; Ebitani. K.; Kaneda, K. Angew. Chem., Int. Ed. 2006, 45, 481-185.
24. (e) Cornell. C. N.; Sigman. M. S. Org. Lett. 2006, 8. 4117-4120.
25. (f) Ref 3f.
26. (g)Ref 3g.
27. (a) Hegedus. L. S.; Allen, G. R; Bozell. J. J.; Waterman. E. L. J. Am. Chem. Soc. 1978, 100, 5800-5807.
28. (b) Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-l. Tetrahedron Lett. 1992, 33, 6643-6646.
29. (c) Larock, R. C; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585.
30. (d) Lei. A.; Liu, G.; Lu, X. LJ)rg. Chem. 2002, 67, 974-980.
31. (e) Bar, G. L. J.; Lloyd-Jones, G. C; Booker -Milbum, K. I. J. Am. Chem. Soc. 2005, 127, 7308-7309.
32. (f) Yip, K.-T.; Yang. M.; Law. K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006,128, 3130-3131.
33. (g) Zhang, Z.; Tan, J.; Wang, Z. Org. Lett. 2008, 10, 173-175.
34. (a) Fix, S. R.; Brice, J. L.: Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164-166.
35. (b) Timokhin, V. I.; Anastasi. N. R.: Stahl. S. S. J. Am. Chem. Soc. 2003, 125, 12996-12997.
36. (c) Brice, J. L.; Harang, J. E.; Timokhin, V. L; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868- 2869.
37. (d) Timokhin, V. L; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 17888- 17893.
38. (e) Rogers, M. M.; Kotov, V.; Chatwichien, J.; Stahl, S. S. Org. Lett. 2007, 9, 4331-4334.
39. (f) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 6328-6335.
40. For Pd-catalvzed cleavage reaction of alkvnes. see: Wang. A.; Jiang. H. J. Am. Chem. Soc. 2008, 130, 5030-5031.
41. Maurya, R.; Singh, R.; Deepak, M.; Handa, S. S.; Yadav, P. P.; Mishra. P. K. Photochemistry 2004, 65, 915-920.
42. Deng. X.; Mani, N. Org. Lett. 2006, 8, 269-272.
43. For representative alkvne oxidation methods, see: (a) Zhu, Z.; Espenson, J. H. J. Org. Chem. 'l995, 60, 7728-7732.
44. (b) Dayan, S.; Ben- David. I.: Rozen. S. J. Org. Chem. 2000, 65, 8816-8818.
45. (c) Murray. R. W.; Singh, M. J. Org. Chem. 1993, 58, 5076-5080.
46. (d) Wolfe, S.: Ingold, C. F. J. Am. Chem. Soc. 1983, 105, 7755-7757.
47. (e) Wan, Z,: Jones, C.D,; Mitchell, D.: Pu, J. Y.; Zhang, T. Y. J. Org. Chem. 2006, 71, 826-828.
48. (f) Yusubov, M. S.: Zholobova, G. A.: Vasilevsky, S. F.: Tretyakov, E. V.; Knight, D. W. Tmrahedron 2002, 58, 1607-1610.
49. (g) Giraud, A.; Provot, O.; Peyrat, J.-F.; Alami, M.; Bnon, J.-D. Tetrahedron 2006, 62, 7667- 7673.
50. (h) Mousset, C: Provot. O.; Hamze, A.: Bignon, J.: Brion, J.-D.; Alami. M. Tetrahedron 2008, 64, 4287-1294.
51. (i) Yusubov, M. S.; Filimonov, V. D. Synthesis 1991, 131-132.
52. (j) Yusubov, M. S.; Kras- nokutskaya. E. A.; Vasilveva. V. P.; Filimonov. V. D.; Chi, K. W. Bull. Korean Chem. Soc. 1995, 16, 86-88.
53. (k) Chi, K.-W.; Yusubov, M. S.; Filimonov, V. D. Synth. Commun. 1994, 24, 2119-2122.
54. (l) Che, C.-M.; Yu, W.-Y,: Chan, P.-M.; Cheng, W.-C: Peng, S.-M.; Lau. K.-C; Li. W.- K. J. Am. Chem. Soc. 2000, 122, 11380-11392.
55. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.