A new Ru catalyst for alkene-alkyne coupling

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7739-7743

  Trost, Barry M ^a   Toste, F Dean ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Alkene addition; Alkyne addition; Atom economy; Carbon carbon bond formation; Ene type addition; Ruthenium catalysis

Indexed keywords

ALKENE; ALKYNE; CARBON; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL MODIFICATION; MOLECULAR INTERACTION;

BETULACEAE;

EID: 0033615744     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01639-1     Document Type: Article

References (22)

1. 1. Trost, B. M. Science 1991, 254, 1471. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
2. 1. Trost, B. M. Science 1991, 254, 1471. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
3. 2. (a) Trost, B. M.; Indolese, A.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
4. (b) Trost, B. M.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 4361.
5. (c) (i) For intramolecular versions catalyzed by Pd, see: Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268 and references cited therein;
6. (ii) by Ti, see: Sturla, S. J.; Kabalaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976;
7. (iii) by Ni-Cr, see: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 6268;
8. (iv) by Ni, see: Radetich, B.; Rajan Babu, T. V. J. Am. Chem. Soc. 1998, 120, 8007.
9. (d) For a review, see: Trost, B. M.; Krische, M. J. Synlett 1998, 1.
10. (e) For related Ru catalyzed reactions, see: Murakami, M.; Ubukata, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 7361.
11. (f) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507.
12. 3. In Ref. 2a, 2-butene was employed to explore mechanism. While it participated to a sufficient extent to establish the mechanistic issue, the reaction was extremely slow and very low yielding - not synthetically useful. All attempts to use disubstituted alkenes with complex 6 were unsatisfactory.
13. 4. Gill, T. P.; Mann, K. R. Organometallics 1982, 1, 485.
14. For a review on Ru catalyzed reactions in organic synthesis, see: Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
15. 5. Other solvents such as methylene chloride, methanol, and toluene resulted in poor or no conversion.
16. 6. For a recent example, see: Grotjahn, D. B.; Joubran, C.; Combs, D.; Brune, D. C. J. Am. Chem. Soc. 1998, 120, 11814. Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488. Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581.
17. 6. For a recent example, see: Grotjahn, D. B.; Joubran, C.; Combs, D.; Brune, D. C. J. Am. Chem. Soc. 1998, 120, 11814. Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488. Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581.
18. 6. For a recent example, see: Grotjahn, D. B.; Joubran, C.; Combs, D.; Brune, D. C. J. Am. Chem. Soc. 1998, 120, 11814. Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488. Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581.
19. 7. Trost, B. M.; Müller, T. J. J.; Martinez, J. A. J. Am. Chem. Soc. 1995, 117, 1888. Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985.
20. 7. Trost, B. M.; Müller, T. J. J.; Martinez, J. A. J. Am. Chem. Soc. 1995, 117, 1888. Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985.
21. 8. Trost, B. M.; Martinez, J. A.; Kulawiec, R. J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402.
22. 9. Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408.