Mixed phosphane η5-CpRuCl(PR3)2 complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes

Journal of the American Chemical Society

Volumn 133, Issue 21, 2011, Pages 8138-8141

  Boeck, Florian ^a   Kribber, Thomas ^a   Xiao, Li ^a   Hintermann, Lukas ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE SOLUTION; CATALYTIC ACTIVITY; HETEROCYCLIC LIGANDS; IN-SITU; PHOSPHANES; TERMINAL ALKYNE;

ACETONE; ALDEHYDES; CATALYST ACTIVITY; HYDRATION;

ACETYLENE;

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; OXAZAPHOSPHORINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; HYDRATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 79957720795     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2026823     Document Type: Article

References (35)

1. Reviews: Hintermann, L.; Labonne, A. Synthesis 2007, 1121
2. Hintermann, L. Top. Organomet. Chem. 2010, 31, 123
3. Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1998, 37, 2867
4. Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Org. Lett. 2001, 3, 735
5. Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am. Chem. Soc. 2001, 123, 11917
6. Grotjahn, D. B.; Incarvito, C. D.; Rheingold, A. L. Angew. Chem., Int. Ed. 2001, 40, 3884
7. Grotjahn, D. B.; Lev, D. A. J. Am. Chem. Soc. 2004, 126, 12232
8. Labonne, A.; Kribber, T.; Hintermann, L. Org. Lett. 2006, 8, 5853
9. Hintermann, L.; Dang, T. T.; Labonne, A.; Kribber, T.; Xiao, L.; Naumov, P. Chem. - Eur. J. 2009, 15, 7167
10. Hintermann, L.; Kribber, T.; Labonne, A.; Paciok, E. Synlett 2009, 2412
11. Labonne, A.; Zani, L.; Hintermann, L.; Bolm, C. J. Org. Chem. 2007, 72, 5704
12. Kribber, T.; Labonne, A.; Hintermann, L. Synthesis 2007, 2809
13. Chevallier, F.; Breit, B. Angew. Chem., Int. Ed. 2006, 45, 1599
14. Nair, R. N.; Lee, P. J.; Rheingold, A. L.; Grotjahn, D. B. Chem. - Eur. J. 2010, 16, 7992
15. Rowlands, G. J. Tetrahedron 2001, 57, 1865
16. Muñiz, K. Angew. Chem., Int. Ed. 2005, 44, 6622
17. Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393
18. Natale, D.; Mareque-Rivas, J. C. Chem. Commun. 2008, 425
19. Grotjahn, D. B. Dalton Trans. 2008, 6497
20. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
21. Kuwata, S.; Ikariya, T. Chem. - Eur. J. 2011, 17, 3542
22. Grotjahn, D. B. Chem. - Eur. J. 2005, 11, 7146
23. Grotjahn, D. B. Chem. Lett. 2010, 39, 908
24. Grotjahn, D. B.; Miranda-Soto, V.; Kragulj, E. J.; Lev, D. A.; Erdogan, G.; Zeng, X.; Cooksy, A. L. J. Am. Chem. Soc. 2008, 130, 20
25. Grotjahn, D. B.; Kragulj, E. J.; Zeinalipour-Yazdi, C. D.; Miranda-Soto, V.; Lev, D. A.; Cooksy, A. L. J. Am. Chem. Soc. 2008, 130, 10860
26. Hintermann, L.; Xiao, L.; Labonne, A.; Englert, U. Organometallics 2009, 28, 5739
27. Hintermann, L.; Xiao, L.; Labonne, A. Angew. Chem., Int. Ed. 2008, 47, 8246
28. 31P NMR analysis.
29. Coordinates have been submitted to the Cambridge Structural Database (CCDC 813354); also see the Supporting Information.
30. df provides no hints regarding potential secondary interactions between the ligand and a coordinated substrate; it probably does not correspond to a reactive conformation.
31. See the Supporting Information for additional data.
32. The acceleration is presumably due to a medium polarity effect that reduces the effects of ion pairing in the catalyst complex.
33. Slow hydration of a cyanoalkyne has been ascribed to nitrile coordination (see ref 3b).
34. d (which are commercially available) were also successful.
35. aa in acetone, (8e) but chloride inhibition was largely absent in the water-rich reaction medium used with our catalyst.