Rhodium-catalyzed selective cross-coupling of internal alkynes with a terminal silylacetylene

Chemistry Letters

Volumn 36, Issue 7, 2007, Pages 830-831

  Katagiri, Takashi ^a   Tsurugi, Hayato ^a   Funayama, Atsushi ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547184427     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.830     Document Type: Article

References (32)

1. a) B. M. Trost, Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
2. b) J. Tsuji, Transition Metal Reagents and Catalysts, Wiley, Chichester, U. K., 2000.
3. B. M. Trost, M. T. Sorum, C. Chan, A. E. Harms, G. Runter, J. Am. Chem. Soc. 1997, 119, 698.
4. a) M. Akita, H. Yasuda, A. Nakamura, Bull. Chem. Soc. Jpn. 1984, 57, 480.
5. b) C. S. Yi, N. Liu, Organometallics 1998, 17, 3158.
6. c) U. Lücking, A. Pfaltz, Synlett 2000, 1261.
7. d) J. Wang, M. Kapon, J. C. Berthet, M. Ephritikhine, M. S. Eisen, Inorg. Chim. Acta 2002, 334, 183.
8. e) L. Chen, C.-J. Li, Tetrahedron Lett. 2004, 45, 2771.
9. f) T. Hirabayashi, S. Sakaguchi, Y. Ishii, Adv. Synth. Catal. 2005, 347, 872.
10. g) H. Katayama, H. Yari, M. Tanaka, F. Ozawa, Chem. Commun. 2005, 4336.
11. a) A. Funayama, T. Satoh, M. Miura, J. Am. Chem. Soc. 2005, 127, 15354, and references therein.
12. b) S. Miyamura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 2255.
13. c) K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407.
14. Very recently similar catalytic reaction of internal alkynes with triphenyland trialkylsilylacetylenes using Rh was independently reported: a) T. Nishimura, K. Onishi, X.-X. Guo, T. Hayashi, The 87th National Meeting of the Chemical Society of Japan, Osaka, March 2007, Abstr. No., 3D6-02. Reaction with Pd.
15. b) S. Ninomiya, Y. Aoyama, N. Tsukada, Y. Inoue, The 87th National Meeting of the Chemical Society of Japan, Osaka, March 2007, Abstr. No., 3D8-34.
16. 16
17. a) C. A. Tolman, Chem. Rev. 1977, 77, 313.
18. b) P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek, P. Dierkes, Chem. Rev. 2000, 100, 2741.
19. a) J. Ohshita, K. Furumori, A. Matsuguchi, M. Ishikawa, J. Org. Chem. 1990, 55, 3277.
20. b) M. Ishikawa, J. Ohshita, Y. Ito, A. Minato, J. Chem. Soc., Chem. Commun. 1988, 804.
21. c) Ru-catalyzed reaction of 1 with tert-butylacetylene; Ref. 3b.
22. The relevant stereoisomers of 5a and 5b (trimethylsilyl group is attached instead of tert-butyldimethylsilyl group) were observed to be formed selectively by the reaction of 4a and 4b with bis(trimethylsilyl) acetylene in the presence of a rhodium catalyst: A. Horita, H. Tsurugi, T. Satoh, M. Miura, The 87th National Meeting of the Chemical Society of Japan, Osaka, March 2007, Abstr. No., 2D8-48.
23. Pd-catalyzed cross-coupling of 2-propyn-1-ols with terminal alkynes: a) B. M. Trost, M. C. McIntosh, J. Am. Chem. Soc. 1995, 117, 7255.
24. b) Ref. 3c.
25. a) R. Shintani, K. Okamoto, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 2872.
26. b) H. Yamabe, A. Mizuno, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 3248.
27. Assignments of the products are shown in Supporting Information.
28. When trimethylsilylacetylene was used in place of 2 in Scheme 3 (at 120°C in a sealed tube), the corresponding (E)-enyne was obtained in 23% yield along with its stereo- and regioisomers (7%).
29. 2,3f
30. Hydrosilylation reactions by rhodium and iridium complexes involving E/Z isomerization: a) C. H. Jun, R. H. Crabtree, J. Organomet. Chem. 1993, 447, 177.
31. b) I. Ojima, N. Clos, R. J. Donovan, P. Ingallina, Organometallics 1990, 9, 3127.
32. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.