Efficient transfer hydrogenation of alkynes and alkenes with methanol catalysed by hydrido(methoxo)iridium(III) complexes

Chemical Communications

Volumn , Issue 18, 1999, Pages 1821-1822

  Tani, Kazuhide ^a   Iseki, Aika ^a   Yamagata, Tsuneaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; HYDROGEN; IRIDIUM COMPLEX; METHANOL;

ARTICLE; CATALYST; HYDROGENATION; REACTION ANALYSIS;

EID: 0033592327     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905765j     Document Type: Article

References (24)

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2. For reviews see: R. A. W. Johnstone, A. H. Wilbi and L. D. Entwisth, Chem. Rev., 1985, 85, 129 ; G. Brieger and T. J. Nestricle, Chem. Rev., 1974, 74, 563 ; R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97.
3. For reviews see: R. A. W. Johnstone, A. H. Wilbi and L. D. Entwisth, Chem. Rev., 1985, 85, 129 ; G. Brieger and T. J. Nestricle, Chem. Rev., 1974, 74, 563 ; R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97.
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11. 3' has been reported: R. Zanella, F. Canziani and M. J. Graziani, J. Organomet. Chem., 1974, 67, 449. For transfer hydrogenation of activated alkenes, see: M. Saburi, M. Ohnuki, M. Ogasawara, T. Takahashi and Y. Uchida, Tetrahedron Lett., 1992, 39, 5783; H. Brunner and W. Leitner, Angew. Chem., Int. Ed. Engl., 1988, 27, 1180.
12. 3' has been reported: R. Zanella, F. Canziani and M. J. Graziani, J. Organomet. Chem., 1974, 67, 449. For transfer hydrogenation of activated alkenes, see: M. Saburi, M. Ohnuki, M. Ogasawara, T. Takahashi and Y. Uchida, Tetrahedron Lett., 1992, 39, 5783; H. Brunner and W. Leitner, Angew. Chem., Int. Ed. Engl., 1988, 27, 1180.
13. 3' has been reported: R. Zanella, F. Canziani and M. J. Graziani, J. Organomet. Chem., 1974, 67, 449. For transfer hydrogenation of activated alkenes, see: M. Saburi, M. Ohnuki, M. Ogasawara, T. Takahashi and Y. Uchida, Tetrahedron Lett., 1992, 39, 5783; H. Brunner and W. Leitner, Angew. Chem., Int. Ed. Engl., 1988, 27, 1180.
14. 3' has been reported: R. Zanella, F. Canziani and M. J. Graziani, J. Organomet. Chem., 1974, 67, 449. For transfer hydrogenation of activated alkenes, see: M. Saburi, M. Ohnuki, M. Ogasawara, T. Takahashi and Y. Uchida, Tetrahedron Lett., 1992, 39, 5783; H. Brunner and W. Leitner, Angew. Chem., Int. Ed. Engl., 1988, 27, 1180.
15. 3' has been reported: R. Zanella, F. Canziani and M. J. Graziani, J. Organomet. Chem., 1974, 67, 449. For transfer hydrogenation of activated alkenes, see: M. Saburi, M. Ohnuki, M. Ogasawara, T. Takahashi and Y. Uchida, Tetrahedron Lett., 1992, 39, 5783; H. Brunner and W. Leitner, Angew. Chem., Int. Ed. Engl., 1988, 27, 1180.
16. 3' has been reported: R. Zanella, F. Canziani and M. J. Graziani, J. Organomet. Chem., 1974, 67, 449. For transfer hydrogenation of activated alkenes, see: M. Saburi, M. Ohnuki, M. Ogasawara, T. Takahashi and Y. Uchida, Tetrahedron Lett., 1992, 39, 5783; H. Brunner and W. Leitner, Angew. Chem., Int. Ed. Engl., 1988, 27, 1180.
17. T. Yamagata, A. Iseki and K. Tani, Chem. Lett., 1997, 1215.
18. K. Tani, A. Iseki and T. Yamagata, Angew, Chem., Int. Ed., 1998, 37, 3381; Angew, Chem., 1998, 110, 3590.
19. K. Tani, A. Iseki and T. Yamagata, Angew, Chem., Int. Ed., 1998, 37, 3381; Angew, Chem., 1998, 110, 3590.
20. 1H NMR and GC-MS.
21. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987, p. 531.
22. 3, 75 MHz) 180.7 (dd, J 11, 123 Hz, CO). Complex 3 can be quantitatively prepared from the reaction of 1 and CO.
23. 2'. Complex 4 can also be obtained as the main product by pyrolysis of complex 2a at 80 °C in methanol-toluene.
24. For isomerisation as well as hydrogenation of alkenes, the same dihydride 5 can also act as a catalyst. Insertion of cis-alkene into Ir-H and subsequent β-hydrogen elimination from the hydrido(alkyl) complex gives trans-alkene and 5, or reductive elimination from the hydrido(alkyl) complex gives alkane and 'Ir(diphosphine)Cl', respectively.