Highly linear-selective hydroformylation of 1-alkenes using formaldehyde as a syngas substitute

Advanced Synthesis and Catalysis

Volumn 352, Issue 2-3, 2010, Pages 299-304

  Makado, Gouki ^a   Morimoto, Tsumoru ^a   Sugimoto, Yasuko ^a   Tsutsumi, Ken ^a   Kagawa, Natsuko ^b   Kakiuchi, Kiyomi ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

Alkenes; Formaldehyde; Homogeneous catalysis; Hydroformylation; Rhodium

Indexed keywords

EID: 77149133370     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.200900713     Document Type: Article

References (27)

1. a) C. Claver, P. W. N. M. van Leeuwen, Rhodium Catalyzed Hydroformylation, Kluwer Academic, Dordrecht, 2000;
2. b) I. Ojima, C. Y. Tsai, M. Tzamarioudaki, D. Bonafoux, in: Organic Reactions, Vol. 56, (Eds.: R. Bittman, E. Ciganek, D. P. Curran, S. E. Denmark, L. S. Hegedus, R. M. Joyce, M. J. Martinelli, S. W. McCombie, L. E. Overman, J. B. Press, L. S. Press, T. V. Rajanbabu, J. H. Rigby, W. R. Roush, A. B. Smith III, P. Wipf), John Wiley & Sons, Inc., New York, 2000, pp 1-354;
3. c) C. D. Frohning, C. W. Kohlpaintner, H. W. Bohnen, in: Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1, (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2002, pp 31-103.
4. For recent reviews, see: a) B. Breit, Top. Curr. Chem. 2007, 279, 139-172;
5. b) R. V. Chaudhari, Curr. Opin. Drug Discovery Dev. 2008, 11, 820-828.
6. O. Roelen, Ger. Offen. 849,548, 1938.
7. a) T. Okano, T. Kobayashi, H. Konishi, J. Kiji, Tetrahedron Lett. 1982, 23, 4967-4968;
8. b) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286-1291;
9. c) H. S. Ahn, S. H. Han, S. J. Uhm, W. K. Seok, H. N. Lee, G. A. Korneeva, J. Mol. Catal. A: Chem. 1999, 144, 295-306;
10. d) M. Rosalez, Á. González, B. González, C. Moratinos, H. Pérez, J. Urdaneta, R. A. Sánchez-Delgado, J. Organomet. Chem. 2005, 690, 3095-3098;
11. e) M. Rosalez, F. Arrieta, P. Baricelli, Á. González, B. González, Y. Guerrero, C. Moratinos, I. Pacheco, H. Pérez, J. Urdaneta, Catal. Lett. 2008, 126, 367-370.
12. For papers on the use of formaldehyde as CO substitute, see: a) K. Fuji, T. Morimoto, K. Tsutsumi, K. Kakiuchi, Angew. Chem. 2003, 115, 2511-2513;
13. Angew. Chem. Int. Ed. 2003, 42, 2409-2411;
14. b) K. Fuji, T. Morimoto, K. Tsutsumi, K. Kakiuchi, Tetrahedron Lett. 2004, 45, 9163-9166;
15. c) K. Fuji, T. Morimoto, K. Tsutsumi, K. Kakiuchi, Chem. Commun. 2005, 3295-3297;
16. d) T. Morimoto, M. Fujioka, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Organomet. Chem. 2007, 692, 625-634;
17. e) T. Morimoto, K. Yamasaki, A. Hirano, K. Tsutsumi, N. Kagawa, K. Kakiuchi, Y. Harada, Y. Fukumoto, N. Chatani, T. Nishioka, Org. Lett. 2009, 11, 1777-1780.
18. Quite recently, Breit and Krische reported on the novel use of formaldehyde in Ru-catalyzed C - C bond formation reaction. In the reaction, formaldehyde acts as the electrophile to the Ru-allyl species. T. Smejkal, H. Han, B. Breit, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 10366-10367.
19. 2, followed by oxidation. D. R. Edwards, C. M. Crudden, K. Yam, Adv. Synth. Catal. 2005, 347, 50-54.
20. M. Kreis, A. Palmelund, L. Bunch, R. Madsen, Adv. Synth. Catal. 2006, 348, 2148-2154.
21. M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1995, 14, 3081-3089.
22. In the reaction mixture, we observed no formation of any anticipated product except for desired aldehydes and isomers of 1-decene; for examples, aldol and Tischenko reaction products of formed aldehydes with them or formaldehyde.
23. a) T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058;
24. b) K. A. Bunten, D. H. Farrar, A. J. Poë, A. Lough, Organometallics 2002, 21, 3344-3350.
25. 31P NMR, an elemental analysis, and X-ray crystallographic analysis, see the Supporting Information.
26. 2 (xantphos): (i) a Rh-xantphos species decarbonylates directly formaldehyde, (ii) the BINAP ligand in Rh(CO) (BINAP) is substituted with xantphos, and (iii) a Rh-xantphos species traps free carbon monoxide formed from the decarbonylation of formaldehyde. A detailed discussion will be presented in the near future.
27. L. A. van der Veen, P. H. Keeven, G. C. Schoemaker, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, M. Luts, A. J. Spek, Organometallics 2000, 19, 872-883.