Catalytic allylic alkylation via the cross-dehydrogenative-coupling reaction between allylic sp3 C-H and methylenic sp3 C-H bonds

Journal of the American Chemical Society

Volumn 128, Issue 1, 2006, Pages 56-57

  Li, Zhiping ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLACETONE; ALLYL COMPOUND; CARBON; COBALT CHLORIDE; COPPER; CYCLOHEXENE DERIVATIVE; HYDROGEN; PALLADIUM; TERT BUTYL HYDROPEROXIDE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 30744478964     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056541b     Document Type: Article

References (23)

1. For representative references, see: (a) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: New York, 2000; Chapter 4, p 109.
2. (b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
3. Negishi, E.-I., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
4. Kazmaier, U.; Pohlman, M. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; De Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 9, p 531.
5. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9728.
6. Trost, B. M.; Strege, P. E.; Weber, L.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3407.
7. (a) Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 3173.
8. (b) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968.
9. (c) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672.
10. (d) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
11. (e) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
12. CAUTION! Mixing a metal salt and peroxide can cause an explosion. See: Jones, A. K.; Wilson, T. E.; Nikam, S. S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; Vol. 2, p 880.
13. The other products are mainly the oxidation products of cyclohexene. We did not find the dialkylation products from the reaction mixture. The following are representative reviews of catalytic allylic C-H oxidation with peroxide. Cu: Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845.
14. Co: Iqbal, J.; Mukhopadhyay, M.; Mandal, A. K. Synlett 1997, 876.
15. For some examples of copper-catalyzed allylic alkylation, see: (a) Kacprzynski, M. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 10676.
16. (b) Van Zijl, A. W.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Adv. Synth. Catal. 2004, 346, 413.
17. (c) Malda, H.; Van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169.
18. For some examples of cobalt-catalyzed allylic alkylation, see: (a) Vallribera, A.; Serra, N.; Marquet, J.; Moreno-Manas, M. Tetrahedron 1993, 49, 6451.
19. (b) Hegedus, L. S.; Inoue, Y. J. Am. Chem. Soc. 1982, 104, 4917.
20. (c) Roustan, J. L.; Merour, J. Y.; Houlihan, F. Tetrahedron Lett. 1979, 20, 3721.
21. Conrow, K. J. Am. Chem. Soc. 1959, 81, 5461.
22. Tenagliu, A.; Kammerer, F. Synlett 1996, 576.
23. Coseri, S.; Ingold, K. U. Org. Lett. 2004, 6, 1641.