Rhodium-catalyzed reaction of terminal alkynes with allylamine leading to (E)-3-alkylidene N-heterocycles

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4641-4643

  Fukumoto, Yoshiya ^a   Kinashi, Fuyuko ^a   Kawahara, Takuya ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750086992     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0619415     Document Type: Article

References (27)

1. For general reviews, see: (a) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59.
2. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197.
3. (c) Cadierno, V.; Gamasa, M. P.; Gimeno, J. Eur. J. Inorg. Chem. 2001, 571.
4. (d) Selegue, J. P. Coord. Chem. Rev. 2004, 248, 1543.
5. For a review on metathesis polymerization catalyzed by vinylideneruthenium complexes, see: Katayama, H.; Ozawa, F. Coord. Chem. Rev. 2004, 248, 1703.
6. For reviews on catalytic reactions that proceeded via vinylidene metal intermediates, see: (a) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507.
7. (b) Bruneau, C.; Dixneuf, P. H. Acc Chem. Res. 1999, 32, 311.
8. (c) Bruneau, C. In Topics in Organometallic Chemistry, Bruneau, C., Dixneuf, P. H., Eds.; Springer: Berlin, 2004; Vol. 11 (Ruthenium Catalysts and Fine Chemistry), p 125.
9. (d) Fishmeister, C.; Bruneau, C.; Dixneuf, P. H. In Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinhelm, 2004, p 189.
10. (e) Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176.
11. For recent examples, see: (a) Davidson, M. H.; McDonald, F. E. Org. Lett. 2004, 6, 1601.
12. (b) Grotjahn, D. B.; Lev, D. A. J. Am. Chem. Soc. 2004, 126, 12232.
13. For reviews on transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes, see: (a) Togni, A., Grützmacher, H., Eds. Catalytic Heterofunctionalization; Wiley-VCH: Weinhehn, 2001.
14. (b) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368.
15. (c) Alonso, F.; Beletskaya, I.; Yus, P. M. Chem. Rev. 2004, 104, 3079.
16. McDonald, F. K.; Chatterjee, A. K. Tetrahedron Lett. 1997, 35, 7687.
17. Fukumoto, Y.; Dohi, T.; Masaoka, H.; Chatani, N.; Murai, S. Organometallics 2002, 21, 3845.
18. Park, Y. J.; Kwon, B.-I.; Ahn, J.-A.; Lee, H.; Jun, C.-H. J. Am. Chem. Soc. 2004, 126, 13892.
19. (a) Shinger, H.; Wilkinson, G. J. Chem. Soc. (A) 1968, 849.
20. (b) Yoshikawa, S.; Kiji, J.; Furukawa, J. Makromol. Chem. 1977, 178, 1077.
21. (c) Carlton, L.; Read, G. J. Chem. Soc., Perkin 1 1978, 1631.
22. For a review on vinylidene-rhodium complexes, see: Werner, H. Coord. Chem. Rev. 2004, 248, 1693.
23. 3 gave 2a in 69% yield for 48 h.
24. For an example of the cationic vinylidene-rhodium complex, see: Windmüller, B. B.; Nürnberg, O.; Wolf, J.; Werner, H. Eur. J. Inorg. Chem. 1999, 613.
25. Wolf, J.; Werner, H.; Serhadli, O.; Ziegler, M. L. Angew. Chem., Int. Ed. 1983, 22, 414.
26. Bianchini, C.; Meli, A.; Peruzini, M.; Zanobini, F. Organometallics 1990, 9, 241.
27. An alternative mechanism involves the formation of another vinylidene-rhodium complex X from II via VIII and IX.