Recent advances in the synthetic and mechanistic aspects of the ruthenium-catalyzed carbon-heteroatom bond forming reactions of alkenes and alkynes

Journal of Organometallic Chemistry

Volumn 696, Issue 1, 2011, Pages 76-80

  Yi, Chae S ^a  

^a Marquette University   (United States)

Author keywords

Alkene; Alkyne; Carbon heteroatom bond; Ruthenium catalyst

Indexed keywords

ACRYLIC COMPOUNDS; ALKENE; ALKYNE; BIFUNCTIONAL; BOND FORMATION; BOND-FORMING REACTIONS; C-O BOND FORMATION; CARBON-HETEROATOM BOND; CARBON-HETEROATOM BONDS; CONJUGATE ADDITION; COUPLING REACTION; ENOL ESTERS; HETEROATOM BONDS; HYDRIDE COMPLEXES; HYDROAMINATIONS; IN-SITU; MECHANISTIC ASPECTS; REGIO-SELECTIVE; RUTHENIUM CATALYST; STEREO-SELECTIVE;

ACETYLENE; CARBOXYLIC ACIDS; CATALYSTS; CHEMICAL BONDS; ESTERS; HYDROSILYLATION; OLEFINS; REACTION KINETICS; RUTHENIUM;

RUTHENIUM COMPOUNDS;

EID: 78649845500     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.08.002     Document Type: Article

References (58)

1. Recent reviews:
2. T.E. Müller, and M. Beller Chem. Rev. 98 1998 675
3. R. Taube B. Cornils, W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds vol. 1 2002 VCH New York
4. J.J. Brunet, and D. Neibecker A. Togni, H. Griitzmacher, Catalytic Heterofunctionalization from Hydroamination to Hydrozirconation 2001 Wiley-VCH New York
5. P.W. Roesky, and T.E. Müller Angew. Chem. Int. Ed. 42 2003 2708
6. J.F. Hartwig Pure Appl. Chem. 76 2004 507
7. T.E. Müller, K.C. Hultzsch, M. Yus, F. Foubelo, and M. Tada Chem. Rev. 108 2008 3795
8. Examples of anti-Markovnikov hydroamination reactions:
9. J.-S. Ryu, G.Y. Li, and T.J. Marks J. Am. Chem. Soc. 125 2003 12584
10. M. Utsunomiya, and J.F. Hartwig J. Am. Chem. Soc. 126 2004 2702
11. M.S. Sanford, and J.T. Groves Angew. Chem. Int. Ed. 43 2004 588
12. H.E. Bryndza, and W. Tam Chem. Rev. 88 1988 1163
13. K. Tani, and Y. Kataoka A. Togni, H. Grützmacher, Catalytic Heterofunctionalization from Hydroamination to Hydrozirconation 2001 Wiley-VCH New York
14. E.M. Beccalli, G. Broggini, M. Martinelli, and S. Sottocornola Chem. Rev. 107 2007 5318
15. B. Marcinec Comprehensive Handbook of Hydrosilylation 1992 Pergamon Oxford
16. K. Yamamoto, and T. Hayashi M. Beller, C. Bolm, Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals vol. 2 2004 Wiley-VCH Weinheim
17. M.A. Brook Silicon in Organic Organometallic and Polymer Chemistry 2000 Wiley New York
18. B. Marciniec, and J. Gulinski J. Organomet. Chem. 446 1993 15
19. H. Nishiyama, and K. Itoh I. Ojima, Catalytic Asymmetric Synthesis 2000 Wiley-VCH New York
20. R.A. Widenhoefer Acc. Chem. Res. 35 2002 905
21. P. Perlmutter Conjugate Addition Reactions in Organic Synthesis 1992 Pergamon Oxford
22. D. Enders, H. Wahl, and W. Bettray Angew. Chem. Int. Ed. 34 1995 455
23. C.S. Yi, S.Y. Yun, and Z. He Organometallics 22 2003 3031
24. D.A. Singleton, and A.A. Thomas J. Am. Chem. Soc. 117 1995 9357
25. D.E. Frantz, D.A. Singleton, and J.P. Snyder J. Am. Chem. Soc. 119 1997 3383
26. V. Nair, and A. Deepthi Chem. Rev. 107 2007 1862
27. J.M. Brown E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis 1999 Springer Berlin
28. T. Ohkuma, M. Kitamura, and R. Noyori I. Ojima, Catalytic Asymmetric Synthesis 2000 Wiley-VCH Weinheim
29. W. Tang, and X. Zhang Chem. Rev. 103 2003 3029
30. Selected review articles:
31. C. Bruneau, and P.H. Dixneuf Acc. Chem. Res. 32 1999 311
32. D. Drozdak, B. Allaert, N. Ledoux, I. Dragutan, V. Dragutan, and F. Verpoort Adv. Synth. Cat 347 2005 1721
33. T. Mitsudo, Y. Hori, Y. Yamakawa, and Y. Watanabe J. Org. Chem. 52 1987 2230
34. H. Doucet, B. Martin-Vaca, C. Bruneau, and P.H. Dixneuf J. Org. Chem. 60 1995 7247
35. L.J. Goossen, J. Paetzold, and D. Koley Chem. Commun. 2003 706
36. J.H.H. Ho, D.S. Black, B.A. Messerle, J.K. Clegg, and P. Turner Organometallics 25 2006 5800
37. J. Le Paih, F. Monnier, S. Dérien, P.H. Dixneuf, E. Clot, and O. Eisenstein J. Am. Chem. Soc. 125 2003 11964
38. K. Cherry, J.-L. Parrain, J. Thibonnet, A. Duchêne, and M. Abarbri J. Org. Chem. 70 2005 6669
39. Y. Wang, and D.J. Burton J. Org. Chem. 71 2006 3859
40. K. Ueura, T. Satoh, and M. Miura Org. Lett. 9 2007 1407
41. H. Kim, S.D. Goble, and C. Lee J. Am. Chem. Soc. 129 2007 1030
42. C.S. Yi, and R. Gao Organometallics 28 2009 6585
43. C. Bruneau, Z. Kabouche, M. Neveux, B. Seiller, and P.H. Dixneuf Inorg. Chim. Acta 222 1994 155
44. A.L. Casalnuovo, J.C. Calabrese, and D. Milstein J. Am. Chem. Soc. 110 1988 6738
45. C.S. Yi, and S.Y. Yun Org. Lett. 7 2005 2181
46. C.S. Yi, S.Y. Yun, and I.A. Guzei Organometallics 23 2004 5392
47. I. Ojima S. Patai, Z. Rappoport, The Chemistry of Organic Silicon Compounds 1989 Wiley New York
48. J. Reichl, and D.H. Berry Adv. Organomet. Chem. 43 1998 197
49. B. Marciniec B. Cornils, W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds vol. 1 2002 VCH New York
50. Y. Wakatsuki, H. Yamazaki, M. Nakano, and Y. Yamamoto Chem. Commun. 1991 703
51. M. Brookhart, and B.E. Grant J. Am. Chem. Soc. 115 1993 2151
52. A.M. LaPointe, F.C. Rix, and M. Brookhart J. Am. Chem. Soc. 119 1997 906
53. C.S. Yi, Z. He, D.W. Lee, A.L. Rheingold, and K.-C. Lam Organometallics 19 2000 2036
54. C.S. Yi, R. Gao, unpublished results.
55. B.M. Trost, and Z.T. Ball J. Am. Chem. Soc. 127 2005 17644
56. B.M. Trost, Z.T. Ball, and K.M. Laemmerhold J. Am. Chem. Soc. 127 2005 10028
57. T.-Y. Luh Pure Appl. Chem. 77 2005 2083
58. H. Mizuno, and J.M. Buriak J. Am. Chem. Soc. 130 2008 17656