Cross-coupling of alkynes catalyzed by phebox-rhodium acetate complexes

Organometallics

Volumn 26, Issue 25, 2007, Pages 6412-6417

  Ito, Jun Ichi ^a   Kitase, Megumi ^a   Nishiyama, Hisao ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; ESTERS; HYDROGEN; SUBSTITUTION REACTIONS; X RAY DIFFRACTION ANALYSIS;

ALKYNES; PHENYLACETYLENE; VINYL COMPLEXES;

RHODIUM COMPOUNDS;

EID: 37249063137     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700742t     Document Type: Article

References (48)

1. (a) Shi Shun, A. L. K.; Tykwinski, R. R. Angew. Chem., Int. Ed. 2006, 45, 1034.
2. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
3. (c) Dai, M.; Sarlah, D.; Yu, M.; Danishefsky, S. J.; Jones, G. O.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 645.
4. (d) Herndon, J. W.; Wang, H. J. Org. Chem. 1998, 63, 4564.
5. (e) Anthony, J.; Boudon, C.; Diederich, F.; Gisselbrecht, J.; Gramlich, V.; Gross, M.; Hobi, H.; Seiler, P. Angew. Chem., Int. Ed. Engl. 1994, 22, 763.
6. (f) Sakamoto, R.; Murata, M.; Nishihara, H. Angew. Chem., Int. Ed. 2006, 45, 4793.
7. (g) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664.
8. (h) Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 4130.
9. (a) Giacomelli, C.; Marcacci, F.; Caporusso, A. M.; Lardicci, L. Tetrahedron Lett. 1979, 3217.
10. (b) Bianchini, C.; Eruzzini, M.; Anobini, F.; Rediani, P.; Lbinati, A. J. Am. Chem. Soc. 1991, 113, 5453.
11. (c) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604.
12. (d) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364.
13. (e) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968.
14. (f) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 75, 2291.
15. (g) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275.
16. (h) Haskel, A.; Wang, J. Q.; Straub, T.; Neyroud, T. G.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3025.
17. (i) Haskel, A.; Straub, T.; Dash, A. K.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3014.
18. (j) Ohmura, T.; Yorozuya, S.; Yamamoto, Y.; Miyaura, N. Organometallics 2000, 19, 365.
19. (k) Esteruelas, M. A.; Herrero, J.; López, A. M.; Oliván, M. Organometallics 2001, 20, 3202.
20. (l) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591.
21. (m) Ogoshi, S.; Ueta, M.; Oka, M.; Kurosawa, H. Chem. Commun. 2004, 2732.
22. (n) Lee, C.-C.; Lin, Y.-C.; Liu, Y.-H.; Wang, Y. Organometallics 2005, 24, 136.
23. (o) Komeyama, K.; Kawabata, T.; Takehira, K.; Takai, K. J. Org. Chem. 2005, 70, 7260.
24. (p) Chen, X.; Xue, P.; Sung, H. H. Y.; Williams, I. D.; Peruzzini, M.; Bianchini, C.; Jia, G. Organometallics 2005, 24, 4330.
25. (q) Weng, W.; Guo, C.; Çelenligil-Çetin, R.; Foxman, B. M.; Ozerov, O. V. Chem. Commun. 2006, 197.
26. (a) Nishiura, M.; Hou, Z.; Wakatsuki, Y.; Yamaki, T.; Miyamoto, T. J. Am. Chem. Soc. 2003, 125, 1184.
27. (b) Liu, Y.; Nishiura, M.; Wang, Y.; Hou, Z. J. Am. Chem. Soc. 2006, 128, 5592.
28. (a) Trost, B. M; Chan, C.; Ruhter, G. J. Am. Chem. Soc. 1987, 109, 3486.
29. (b) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
30. (c) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158.
31. (d) Chen, L.; Li, C.-J. Terahedron Lett. 2004, 45, 2771.
32. (e) Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2005, 347, 872.
33. (a) Akita, M.; Yasuda, H.; Nakamura, A. Bull. Chem. Soc. Jpn. 1984, 57, 480.
34. (b) Katayama, H.; Yari, H.; Tanaka, M.; Ozawa, F. Chem. Commun. 2005, 4336.
35. (c) Wang, J.; Kapon, M.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. Inorg. Chim. Acta 2002, 334, 183.
36. Ito, J.; Nishiyama, H. Eur J. Inorg. Chem. 2007, 1114.
37. Recent examples for C - H activation promoted by an acetate ligand: (a) Ziatdinov, V. R.; Oxgaard, J.; Mironov, O. A.; Young, K. J. H.; Goddard, W. A., III; Periana, R. A. J. Am. Chem. Soc. 2006, 128, 7404.
38. (b) Davies, D. L.; Donald, S. M. A.; Al-Duaij, O.; Macgregor, S. A.; Polleth, M. J. Am. Chem. Soc. 2006, 128, 4210.
39. As for an alternative mechanism, producing enyne via reductive elimination of an acetylide-vinyl complex, see refs 2p and 4e and: (a) Werner, H.; Kukla, F.; Steiner, P. Eur. J. Inorg. Chem. 2002, 1377.
40. (b) Schäfer, M.; Wolf, J.; Werner, H. Organometallics 2004, 23, 5713.
41. (c) Ghosh, F.; Zhang, X.; Achord, P.; Emge, T. J.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 2007, 129, 853.
42. (a) Brothers, P. J. Prog. Inorg. Chem. 1981, 28, 1.
43. (b) King, R. E., III; Busby, D. C.; Hawthorne, M. F. J. Organomet. Chem. 1985, 279, 103.
44. (a) Strauss, S. H.; Whitmire, K. H.; Shriver, D. H. J. Organomet. Chem. 1979, 174, C59.
45. (b) Grushin, V. V.; Kuznetsov, V. F.; Bensimon, C.; Alper, H. Organometallics 1995, 14, 3927.
46. (a) Ito, J.; Shiomi, T.; Nishiyama, H. Adv. Synth. Catal. 2006, 348, 1235.
47. (b) Kanazawa, Y.; Nishiyama, H. Synlett 2006, 3343.
48. Hendrickson, J. B. J. Am. Chem. Soc. 1961, 83, 2018.