Low-pressure hydrogenation of arenecarboxylic acids to aryl aldehydes

Advanced Synthesis and Catalysis

Volumn 352, Issue 13, 2010, Pages 2166-2170

  Gooßen, Lukas J ^a   Khan, Bilal Ahmad ^a   Fett, Thomas ^b   Treu, Matthias ^b  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

^b BOEHRINGER INGELHEIM RCV GMBH AND CO KG   (Austria)

Author keywords

Aldehydes; Carboxylic acids; Catalysis; Hydrogenation; Palladium

Indexed keywords

EID: 77956915837     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000418     Document Type: Article

References (26)

1. B. M. Trost, Comprehensive Organic Synthesis, Pergamon, Oxford, 1991, Vol. 8, pp 259-305.
2. Aluminium hydride derivatives:
3. a) L. I. Zakharkin, V. V. Gavrilenko, D. N. Maslin, I. M. Khorlina, Tetrahedron Lett. 1963, 2087-2090;
4. b) H. C. Brown, P. M. Weissman, J. Org. Chem. 1966, 31, 283-287;
5. S. Chandrasekhar, M. S. Kumar, B. Muralidhar, Tetrahedron Lett. 1998, 39, 909-910;
6. . Muraki, T. Mukaiyama, Chem. Lett. 1974, 1447-1450.
7. Boron hydride derivatives: a) thexylchloroborane-dimethyl sulfide: H. C. Brown, J. S. Cha, N. M. Yoon, N. Behrooz, J. Org. Chem. 1987, 52, 5400-5406;
8. b) boranedimethyl sulfide/PCC: H. C. Brown, CG. Rao, S.U. Kulkami, Synthesis 1979, 704-705.
9. Other reducing agents: a) isobutylmagnesium bromide/ dichlorobis(jt- cyclopentadienyl)titanium: F. Sato, T. Jinbo, M. Sato, Synthesis 1981, 871;
10. b) stannous chloride/ HCl: H. Stephen, J. Chem. Soc. 1925, 1874-1877;
11. triethylsilane: T. Fukuyama, S. C. Lin, L. Li, J. Am. Chem. Soc. 1990, 112, 7050-7051;
12. lithium/methylamine: A. O. Bedenbaugh, J. H. Badenbaugh, W. A. Bergin, J. D. Adkins, J. Am. Chem. Soc. 1970, 92, 5774-5775;
13. e) heterogeneous catalysts: T. Yokoyama, N. Fujita, Appl. Catal. A: General 2004, 276, 179-185.
14. a) K. W. Rosenmund, Ber. Dtsch. Chem. Ges. 1918, 51, 585-593;
15. b) E. Mosettig, Org. React. 1948, 4, 362-377;
16. J. J. Li, Name Reactions, 2nd edn., Springer, Berlin 2003, p 343.
17. a) K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu, A. Yamamoto, Chem. Lett. 1995, 367-368;
18. b) K. Nagayama, I. Shinizu, A. Yamamoto, Chem. Lett. 1998, 1143-1144;
19. K. Nagayama, I. Shinizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 2001, 74,1803-1815.
20. For reactions based on similar concepts, see:
21. a) L. J. Gooßen, K. Ghosh, Angew. Chem. 2001, 113, 35663568;
22. Angew. Chem. Int. Ed. 2001, 40, 3458-3460;
23. b) R Kakino, H. Narahashi, I. Shimizu, A. Yamamoto, Chem. Lett. 2001, 12, 1242-1243;
24. L.J. Gooßen, J. Paetzold, L. Winkel, Synlett 2002, 10, 1721-1723;
25. L. J. Gooßen and K. Ghosh, Chem. Commun. 2001, 2084-2085.
26. L. J. Gooßen, K. Ghosh, Chem. Commun. 2002, 836-837.