Cationic Rh(I)/modified-BINAP-catalyzed reactions of carbonyl compounds with 1,6-diynes leading to dienones and ortho-functionalized aryl ketones

Organic Letters

Volumn 9, Issue 11, 2007, Pages 2203-2206

  Tanaka, Ken ^a   Otake, Yousuke ^a   Wada, Azusa ^a   Noguchi, Keiichi ^a   Hirano, Masao ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34250645784     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0707721     Document Type: Article

References (44)

1. For recent reviews, see: (a) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
2. (b) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
3. (c) Varela, J. A.; Saá, C. Chem. Rev. 2003, 103, 3787.
4. For the use of stoichiometric cobalt reagents, see: (a) Harvey, D. F.; Johnson, B. M.; Ung, C. S.; Vollhardt, K. P. C. Synlett 1989, 15-18.
5. (b) Gleiter, R.; Schehlmann, V. Tetrahedron Lett. 1989, 30, 2893.
6. For the use of stoichiometric zirconacyclopentadienes, see: Takahashi, T.; Li, Y.; Ito, T.; Xu, F.; Nakajima, K.; Liu, Y. J. Am. Chem. Soc. 2002, 124, 1144.
7. Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. J. Am. Chem. Soc. 1988, 110, 8570.
8. Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 6844.
9. For Ru(II)-catalyzed hydrative cyclization and [4 + 2] cycloaddition of yne-enones, see: Trost, B. M.; Brown, R. E.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 5877.
10. Tekevac, T. N.; Louie, J. Org. Lett. 2005, 7, 4037.
11. For Ni-catalyzed [4 + 2 + 2] cycloaddition of 1,6-diynes with cyclobutanones, see: Murakami, M.; Ashida, S.; Matsuda, T. J. Am. Chem. Soc. 2006, 128, 2166.
12. Bennacer, B.; Fujiwara, M.; Lee, S.-Y.; Ojima, I. J. Am. Chem. Soc. 2005, 127, 17756.
13. Kong, J. R.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16040.
14. For examples of carbonyl insertion into a Rh - C bond, see: (a) Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1674.
15. (b) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298.
16. (a) Tanaka, K.; Wada, A.; Noguchi, K. Org. Lett. 2005, 7, 4737.
17. (b) Tanaka, K.; Wada, A.; Noguchi, K. Org. Lett. 2006, 8, 907.
18. (c) Tanaka, K.; Suzuki, N.; Nishida, G. Eur. J. Org. Chem. 2006, 3917.
19. (d) Wada, A.; Noguchi, K.; Hirano, M; Tanaka, K. Org. Lett. 2007, 9, 1295.
20. Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron Lett. 1991, 32, 7283.
21. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
22. Marvell, E. N.; Caple, G.; Gosink, T. A.; Zimmer, G. J. Am. Chem. Soc. 1966, 88, 619.
23. (a) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697.
24. (b) Tanaka, K.; Nishida, G.; Wada, A.; Noguchi, K. Angew. Chem., Int. Ed. 2004, 43, 6510.
25. (c) Tanaka, K.; Toyoda, K.; Wada, A.; Shirasaka, K.; Hirano, M. Chem. - Eur. J. 2005, 11, 1145.
26. (d) Tanaka, K.; Nishida, G.; Ogino, M.; Hirano, M.; Noguchi, K. Org. Lett. 2005, 7, 3119.
27. (e) Nishida, G.; Suzuki, N.; Noguchi, K.; Tanaka, K. Org. Lett. 2006, 8, 3489.
28. (f) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586.
29. (g) Tanaka, K.; Sagae, H.; Toyoda, K.; Noguchi, K; Hirano, M. J. Am. Chem. Soc. 2007, 129, 1522.
30. The use of (R)-Segphos as a ligand furnished 6 with < 10% ee.
31. For Rh-catalyzed C-H arylation of anisole and 1,3-dimethoxybenzene with an aryl iodide, see: Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748.
32. For recent reviews of transition-metal-catalyzed C-H bond activation, see: (a) Dyker, G., Ed. Handbook of C-H Transformations; Wiley-VCH: Weinheim, Germany, 2005.
33. (b) Godula, K.; Sanies, D. Science 2006, 312, 67.
34. (c) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
35. (d) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
36. For selected recent examples of Rh-catalyzed aryl C - H bond functionalization, see: (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202.
37. (b) Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
38. (c) Wang, X.; Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996.
39. (d) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.
40. (e) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332-5333.
41. (f) Also see ref 18.
42. Aryl C - H activation, electrophilic aromatic substitution, and carbopalladation with a Pd(II) complex are proposed in the Pd-catalyzed direct o-C - H functionalization of α-chloroacetanilides: Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
43. For Ru-catalyzed direct o-C - H activation of aryl ketones, see: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
44. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.