Palladium Catalysis for Oxidative 1,2-Difunctionalization of Alkenes

Catalyzed Carbon-Heteroatom Bond Formation

Volumn , Issue , 2010, Pages 119-135

  Jacques, Béatrice ^a   Muñiz, Kilian ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

Aminoacetoxylation; Aminohalogenation; Dialkoxylation; Diamination; Halogenation; Oxidative 1,2 difunctionalization; Palladium catalysis

Indexed keywords

EID: 84883985120     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527633388.ch4     Document Type: Chapter

References (52)

1. Tsuji, J. (2004) Palladium Reagents and Catalysts, Wiley, New York;
2. Bäckvall, J.-E.
3. Bäckvall, J.-E. (1983) Acc. Chem. Res., 16, 335.
4. Coleman, J.L., Hegedus, L.S., Noton, J.R., and Finke, R.G. (1987) Principles and Applications of Transition-Metal Chemistry
5. Canty, A.J. (1992) Acc. Chem. Res., 25, 83.
6. Muñiz, K. (2009) Angew. Chem. Int. Ed., 48, 9412.
7. Stangl, H. and Jira, R. (1970) Tetrahedron Lett., 11, 3589;
8. Hamed, O. and Henry, P.M. (1998) Organometallics, 17, 5184.
9. Bar, G.L.J., Lloyd-Jones, G.C., and Booker-Milburn, K.I. (2005) J. Am. Chem. Soc., 127, 7308;
10. Du, H., Zhao, B., and Shi, Y. (2007) J. Am. Chem. Soc., 129, 762;
11. Du, H., Yuan, W., Zhao, B., and Shi, Y. (2007) J. Am. Chem. Soc., 129, 7496;
12. Du, H., Yuan, W., Zhao, B., and Shi, Y. (2007) J. Am. Chem. Soc., 129, 11688;
13. Yuan, W., Du, H., Zhao, B., and Shi, Y. (2007) Org. Lett., 9, 2589;
14. Xu, L., Du, H., and Shi, Y. (2007) J. Org. Chem., 72, 7038 (g) Xu, L. and Shi, Y. (2008) J. Org. Chem., 73, 749.
15. Xu, L. and Shi, Y. (2008) J. Org. Chem., 73, 749.
16. Bäckvall, J.E. (2004) in Metal-Catalyzed Cross-Coupling Reactions (eds A. de Meijere and F. Diederich), Wiley-VCH, Weinheim, pp. 479-529.
17. Yip, K.-T., Yang, M., Law, K.-L., Zhu, N.-Y., and Yang, D. (2006) J. Am. Chem. Soc., 128, 3130;
18. Welbes, L.L., Lyons, T.W., Cychosz, K.A., and Sanford, M.S. (2007) J. Am. Chem. Soc., 129, 5836;
19. Tong, X., Beller, M., and Tse, M.K. (2007) J. Am. Chem. Soc., 129, 4906;
20. Scarborough, C.C. and Stahl, S.S. (2006) Org. Lett., 8, 3251.
21. Henry, P.M. (ed.) (1980) Palladium Catalyzed Oxidation of Hydrocarbons, Reidel, Dordrecht.
22. El-Qisairi, A., Hamed, O., and Henry, P.M. (1998) J. Org. Chem., 63, 2790;
23. El-Qisairi, A. and Henry, P.M. (2000) J. Organomet. Chem., 603, 50;
24. El-Qisairi, A., Qaseer, H., and Henry, P.M. (2002) J. Organomet. Chem., 656, 167.
25. El-Qisairi, A., Qaseer, H., Katsigras, G., Lorenzi, P., Trivedi, U., Tracz, S., Hartman, A., Miller, J.A., andHenry, P.M. (2003) Org. Lett., 5, 439.
26. Minatti, A. and Muñiz, K. (2007) Chem. Soc. Rev., 36, 1142.
27. Tamaru, Y., Hojo, M., Higashimura, H., andYoshida, Z.-i. (1988) J. Am. Chem. Soc., 110, 3994.
28. Manzoni, M.R., Zabawa, T.P., Kasi, D., and Chemler, S.R. (2004) Organometallics, 23, 5618.
29. Lei, A., Lu, X., and Liu, G. (2004) Tetrahedron Lett., 45, 1785.
30. Szolcsanyi, P. and Gracza, T. (2006) Tetrahedron, 62, 8498.
31. Michael, F.E., Sibbald, P.A., and Cochran, B.M. (2008) Org. Lett., 10, 793.
32. Michael, F.E. and Cochran, B.M. (2006) J. Am. Chem. Soc., 128, 4246.
33. Helaja, J. and Göttlich, R. (2002) Chem. Commun., 720.
34. Antunes, A.M.M., Marto, S.J.L., Branco, P.S., Prabhakar, S., and Lobo, A.M. (2001) Chem. Commun., 405.
35. Antunes, A.M.M., Bonifacio, V.D.B., Nascimento, S.C.C., Lobo, A.M., Branco, P.S., and Prabhakar, S. (2007) Tetrahedron, 30, 7009;
36. Bäckvall, J.E. (1977) J. Chem. Soc., Chem. Commun., 413.
37. Han, J., Li, Y., Zhi, S., Pan, Y., Timmons, C., and Li, G. (2006) Tetrahedron Lett., 47, 7225.
38. Wu, T., Yin, G., and Liu, G. (2009) J. Am. Chem. Soc., 131, 16354.
39. Chevrin, C., Le Bras, J., Henin, F., and Muzart, J. (2005) Synthesis, 2615.
40. Thiery, E., Chevrin, C., Le Bras, J., Harakat, D., and Muzart, J. (2007) J. Org. Chem., 72, 1859.
41. Schultz, M.J. and Sigman, M.S. (2006) J. Am. Chem. Soc., 128, 1460.
42. Zhang, Y. and Sigman, M.S. (2007) J. Am. Chem. Soc., 129, 3076.
43. Li, Y., Song, D., and Dong, V.M. (2008) J. Am. Chem. Soc., 130, 2962.
44. Alexanian, E.J., Lee, C., and Sorensen, E.J. (2005) J. Am. Chem. Soc., 127, 7690.
45. Liu, G. and Stahl, S.S. (2006) J. Am. Chem. Soc., 128, 7179.
46. Hövelmann, C.H., Streuff, J., Brelot, L., and Muñiz, K. (2008) Chem. Commun., 2334.
47. Muñiz, K.,Hövelmann, C.H., and Streuff, J. (2008) J. Am. Chem. Soc., 130, 763.
48. Desai, L.V. and Sanford, M.S. (2007) Angew. Chem. Int. Ed., 46, 5737.
49. Streuff, J., Hövelmann, C.H., Nieger, M., and Muñiz, K. (2005) J. Am. Chem. Soc., 127, 14587.
50. Muñiz, K. (2007) J. Am. Chem. Soc., 129, 14542.
51. Muñiz, K., Hövelmann, C.H., Campos-Gómez, E., Barluenga, J., Gonzalez, J.M., Streuff, J., and Nieger, M. (2008) Chem. Asian J., 3, 776.
52. Muñiz, K., Streuff, J., Chavez, P., and Hövelmann, C.H. (2008) Chem. Asian J., 3, 1245.