Ruthenium(IV) complexes featuring p,O-chelating ligands: Regioselective substitution directly from allylic alcohols

Angewandte Chemie - International Edition

Volumn 49, Issue 15, 2010, Pages 2782-2785

  Sundararaju, Basker ^a   Achard, Mathieu ^a   Demerseman, Bernard ^a   Toupet, Loic ^b   Sharma, Gangavaram V M ^c   Bruneau, Christian ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Allylic compounds; Homogeneous catalysis; P O chelate; Phosphorus; Ruthenium

Indexed keywords

CATALYSIS; CHELATION; LIGANDS; PHOSPHORUS; REGIOSELECTIVITY; RUTHENIUM;

ALLYLIC ALCOHOL; ALLYLIC COMPOUNDS; CHELATING LIGANDS; HOMOGENEOUS CATALYSIS; PRECATALYSTS; REGIO-SELECTIVE; REGIOSELECTIVE SUBSTITUTION;

RUTHENIUM COMPOUNDS;

EID: 77950478482     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200907034     Document Type: Article

References (44)

1. a) Comprehensive Organic Synthesis, Vol.4 (Eds.: S.A. God-leski, B. M. Trost, I. Fleming), Pergamon, New York, 1991, pp. 585-661;
2. b)J. Tsuji, Transition Metal Reagents and Cata-lysts: Innovations in Organic Synthesis, Wiley, Chichester, 2000, p. 109:
3. c) B. M. Trost, M. L. Crawley. Chem. Rev. 2003, 103, 2921;
4. d) G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336.
5. a) H. Saburi, S. Tanaka, M. Kitamura, Angew. Chem. 2005, 117, 1758;
6. Angew. Chem. Int. Ed. 2005, 44, 1730;
7. b)S. Tanaka, H. Saburi, M. Kitamura, Adv. Synth. Catal. 2006, 348, 375;
8. c) S. Tanaka, T. Seki, M. Kitamura, Angew. Chem. 2009, 121, 9110;
9. Angew. Chem. Int. Ed. 2009, 48. 8948.
10. a) A. B. Zaitsev, S. Gruber, P. S. Pregosin, Chem. Commun. 2007, 4692;
11. b) S. Gruber, A.B. Zaitsev, M. Wörle, P.S. Pregosin, Organometallics 2008, 27, 3796;
12. c) I. F. Nieves, D. Schott, S. Gruber. P. S. Pregosin, Helv. Chim. Acta 2007, 90, 271.
13. a) J. A. van Rijn, M. Lutz, L. S. von Chrzanowski, A. L. Spek. E. Bouwman, E. Drent, Adv. Synth. Catal. 2009, 357, 1637:
14. b) J. A. van Rijn, M. A. Siegler, A. L. Spek, E. Bouwman, E. Drent, Organometattics 2009, asap.
15. A. B. Zaitsev, S. Gruber, P. A. Plüss, P. S. Pregosin, L. F. Veiros, M. Wörle, J. Am. Chem. Soc. 2008, 130, 11604.
16. a) A. B. Zaitsev, H. F. Caldwell, P. S. Pregosin, L. F. Veiros, Chem. Eur. J. 2009, 15, 6468;
17. b) S. Gruber, A. B. Zaitsev, M. Wörle, P. S. Pregosin, Organometallics 2009, 28, 3437.
18. a) M. Kawatsura, F. Ata, S. Wada, S. Hayase, H. Uno, T. Itoh, Chem. Commun. 2007, 298:
19. b) M. Kawatsura, F. Ata, T. Hirakawa, S. Hayase. T. Itoh, Tetrahedron Lett. 2008. 49, 4873.
20. a) A. T. Brandvold. US Pat. US5760286. 1998;
21. b) E. Drent. W Sjardijn, J. C. L. J. Suykerbuyk, K. Wanninger, World Pat. 00/ 06615, 2000;
22. c) W. Weng, Z. Shen, R. F. Jordan, J. Am. Chem. Soc. 2007, 129, 15450.
23. For selected references see: a) E. Drent, R. van Dijk, R. van Ginkel, B. van Oort, R. I. Pugh. Chem. Commun. 2002, 744;
24. b) W. Weng, Z. Shen. R. F. Jordan, J. Am. Chem. Soc. 2007, 129, 15450:
25. c) T. Kochi. S. Noda, K. Yoshimura, K. Nosaki. J. Am. Chem. Soc. 2007, 129, 8948;
26. d) L. Betucci, C. Bianchini, C. Claver, E. J. Garcia Suarez, A. Ruiz, A. Meli, W. Oberhauser, Dalton Trans 2007, 5590;
27. e) S. Liu, S. Borkar, D. Newsham, H. Yennawar, A. Sen, Organometattics 2007. 26, 210;
28. f) A. Naka-mura, K. Munakata, T. Kochi, K. Nozaki, J. Am. Chem. Soc. 2008, 130, 81128.
29. L. Bettucci, C. Bianchini. A. Meli. W. Oberhauser, J. Mol. Catal. A 2008, 291, 57.
30. T. Schultz, A. Pfaltz, Synthesis 2005, 1005.
31. a) A. M. McNair, D.C. Boyd, K. R. Mann, Organometallics 1986, 5. 303;
32. b) B. M. Trost, P.L. Fraisse, Z.T. Ball, Angew. Chem. 2002, 114, 1101;
33. Angew. Chem. Int. Ed. 2002. 41, 1059.
34. 2 = 0.989. CCDC 727698 (B-MeOH) contains the supplementary crystal-lography data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
35. a) C. Bruneau, J.-L. Renaud, B. Demerseman, Chem. Eur. J. 2006, 12, 5178;
36. b) R. Hermatschweiler, I. Fernandez, P.S. Pregosin. E. J. Watson, A. Albinati, S. Rizzato, L. F. Veiros, M. J. Calhorda, Organometallics 2005, 24, 1809.
37. 2; = 0.911. CCDC 726159 (C) contains the supplementary crys-tallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif .
38. a) H. J. Zhang, B. Demerseman, L. Toupet, Z. Xi, C. Bruneau, Adv. Synth. Catal. 2008, 350, 1601;
39. b) M. Achard, N. Derrien, H.J. Zhang, B. Demerseman, C. Bruneau, Org. Lett. 2009, 11, 185;
40. c) H. J. Zhang, B. Demerseman. L. Toupet, Z. Xi, C. Bruneau, Organometallics 2009, 28. 5173;
41. d) B. Sundararaju. M. Achard, G. V. M. Sharma, C. Bruneau, Org. Biomol. Chem. 2009, 7, 3906.
42. see supporting information for details.
43. For dicationic allyl ruthenium complexes see: M. D. Mbaye, B. Demerseman, J. L. Renaud. L. Toupet. C. Bruneau, Angew. Chem. 2003, 115, 5220;
44. Angew. Chem. Int. Ed. 2003, 42, 5066.