Ruthenium-catalysed transfer hydrogenation of aromatic aldehydes with dioxane under KOH: Assistance of Cannizzaro reaction

Journal of Chemical Research - Part S

Volumn , Issue 6, 2003, Pages 368-369

  Kim, Bok Tae ^a   Cho, Chan Sik ^a   Kim, Tae Jeong ^a   Shim, Sang Chul ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Alcohols; Aldehydes; Cannizzaro reaction; Ruthenium catalyst; Transfer hydrogenation

Indexed keywords

ALDEHYDE DERIVATIVE; DIOXANE; POTASSIUM HYDROXIDE; RUTHENIUM;

ARTICLE; CANNIZZARO REACTION; CATALYSIS; HYDROGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0141679207     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823403103174173     Document Type: Article

References (21)

1. M. Hudlický, Reductions in Organic Chemistry, American Chemical Society, Washington, DC, 1986.
2. For recent reviews, see: R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97; T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599; M. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045.
3. For recent reviews, see: R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97; T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599; M. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045.
4. For recent reviews, see: R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97; T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599; M. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045.
5. Formation of indoles: C.S. Cho, H.K. Lim, S.C. Shim, T.-J. Kim and H.-J. Choi, Chem. Commun., 1998, 995; C.S. Cho, J.H. Kim and S.C. Shim, Tetrahedron Lett., 2000, 41, 1811; C.S. Cho, J.H. Kim, T.-J. Kim and S.C. Shim, Tetrahedron, 2001, 57, 3321.
6. Formation of indoles: C.S. Cho, H.K. Lim, S.C. Shim, T.-J. Kim and H.-J. Choi, Chem. Commun., 1998, 995; C.S. Cho, J.H. Kim and S.C. Shim, Tetrahedron Lett., 2000, 41, 1811; C.S. Cho, J.H. Kim, T.-J. Kim and S.C. Shim, Tetrahedron, 2001, 57, 3321.
7. Formation of indoles: C.S. Cho, H.K. Lim, S.C. Shim, T.-J. Kim and H.-J. Choi, Chem. Commun., 1998, 995; C.S. Cho, J.H. Kim and S.C. Shim, Tetrahedron Lett., 2000, 41, 1811; C.S. Cho, J.H. Kim, T.-J. Kim and S.C. Shim, Tetrahedron, 2001, 57, 3321.
8. Formation of quinolines: C.S. Cho, B.H. Oh and S.C. Shim, Tetrahedron Lett., 1999, 40, 1499; C.S. Cho, J.S. Kim, B.H. Oh, T-J. Kim, S.C. Shim and N.S. Yoon, Tetrahedron, 2000, 56, 7747; C.S. Cho, B.H. Oh, J.S. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2000, 1885; C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2001, 2576; C.S. Cho, T.K. Kim, B.T. Kim, T.-J. Kim and S.C. Shim, J. Organomet. Chem., 2002, 650, 65.
9. Formation of quinolines: C.S. Cho, B.H. Oh and S.C. Shim, Tetrahedron Lett., 1999, 40, 1499; C.S. Cho, J.S. Kim, B.H. Oh, T-J. Kim, S.C. Shim and N.S. Yoon, Tetrahedron, 2000, 56, 7747; C.S. Cho, B.H. Oh, J.S. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2000, 1885; C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2001, 2576; C.S. Cho, T.K. Kim, B.T. Kim, T.-J. Kim and S.C. Shim, J. Organomet. Chem., 2002, 650, 65.
10. Formation of quinolines: C.S. Cho, B.H. Oh and S.C. Shim, Tetrahedron Lett., 1999, 40, 1499; C.S. Cho, J.S. Kim, B.H. Oh, T-J. Kim, S.C. Shim and N.S. Yoon, Tetrahedron, 2000, 56, 7747; C.S. Cho, B.H. Oh, J.S. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2000, 1885; C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2001, 2576; C.S. Cho, T.K. Kim, B.T. Kim, T.-J. Kim and S.C. Shim, J. Organomet. Chem., 2002, 650, 65.
11. Formation of quinolines: C.S. Cho, B.H. Oh and S.C. Shim, Tetrahedron Lett., 1999, 40, 1499; C.S. Cho, J.S. Kim, B.H. Oh, T-J. Kim, S.C. Shim and N.S. Yoon, Tetrahedron, 2000, 56, 7747; C.S. Cho, B.H. Oh, J.S. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2000, 1885; C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2001, 2576; C.S. Cho, T.K. Kim, B.T. Kim, T.-J. Kim and S.C. Shim, J. Organomet. Chem., 2002, 650, 65.
12. Formation of quinolines: C.S. Cho, B.H. Oh and S.C. Shim, Tetrahedron Lett., 1999, 40, 1499; C.S. Cho, J.S. Kim, B.H. Oh, T-J. Kim, S.C. Shim and N.S. Yoon, Tetrahedron, 2000, 56, 7747; C.S. Cho, B.H. Oh, J.S. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2000, 1885; C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, Chem. Commun., 2001, 2576; C.S. Cho, T.K. Kim, B.T. Kim, T.-J. Kim and S.C. Shim, J. Organomet. Chem., 2002, 650, 65.
13. C.S. Cho, B.T. Kim, M.J. Lee, T.-J. Kim and S.C. Shim, Angew. Chem., Int. Ed., 2001, 40, 958.
14. C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, J. Org. Chem., 2001, 66, 9020; C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, Tetrahedron Lett., 2002, 43, 7987.
15. C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, J. Org. Chem., 2001, 66, 9020; C.S. Cho, B.T. Kim, T.-J. Kim and S.C. Shim, Tetrahedron Lett., 2002, 43, 7987.
16. Strong bases are frequently used as cocatalysts to promote transition metal-catalysed transfer hydrogenation: see ref 2.
17. H. Imai, T. Nishiguchi and K. Fukuzumi, J. Org. Chem., 1976, 41, 665.
18. T.A. Geissman, Organic Reactions, ed. R. Adams, Wiley, New York, 1996, Vol. 2, pp. 94-113.
19. M.K. Anwer, D.B. Sherman, J.G. Roney and A.F. Spatola, J. Org. Chem., 1989, 54, 1284.
20. M.E. Cucullu, S.P. Nolan, T.R. Belderrain and R.H. Grubbs, Organometallics, 1999, 18, 1299.
21. D.H. Lee, S.I. Kim, J.H. Jun, Y.H. Oh and S.K. Kam, J. Korean Chem. Soc., 1997, 41, 639.