Microwaves make hydroformylation a rapid and easy process

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3725-3727

  Petricci, Elena ^a   Mann, André ^c   Schoenfelder, Angèle ^c   Rota, Andrea ^b   Taddei, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b CEM Italia srl   (Italy)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748606917     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061312v     Document Type: Article

References (22)

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2. Rhodium Catalyzed Hydroformylation; van Leeuwen, P. W. N. M., Claver, C., Eds.; Kluwer Academic Publishing: London, U.K., 2000.
3. Siegel, H.; Himmele, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 178.
4. Cornils, B.; Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1994, 33, 2144.
5. Cornils, B.; Hermann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, Germany, 1996.
6. Kovacs, I.; Ungva'ry. F. Coord. Chem. Rev. 1997, 161.
7. Bizzarri, S. N.; Fenelon, S.; Ishikawa-Yamaki, M. Chemical Economics Handbook; SRI International: Menlo Park. 1999; pp 682.7000A.
8. Ojima, I.; Tsai, C.-Y.; Tzamarioudaki, M.; Bonafoux, D. Org. React. 2000, 56, 1.
9. Breit, B.; Seiche, W. Synthesis 2001, 1.
10. Eilbracht, P.; Bartacker, L.; Buss, C.; Hollmann, C.; Kitsos-Rzychon, B.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.; Schmidt, A. Chem. Rev. 1999, 99, 3329.
11. Pino, P.; Botteghi, C. Org. Synth Coll. VI, 1986, 338.
12. Breit, B. Acc. Chem. Res. 2003, 36, 264.
13. Seiche, W.; Schuschkowski, A.; Breit, B. Adv. Svnth. Catal. 2005, 347, 1488.
14. Breit, B.; Seiche, W. J. Am. Chem. Soc. 2003, 125, 6608. To our knowledge, this ligand is not commercially available: search done on Chmoogle web site (www.chmoogle.com). Moreover, the process required from 20 to 90 h to go to completion.
15. Minetto, G.; Raveglia, L. F.; Taddei, M. Org. Lett. 2004, 6, 389.
16. Dessole, G.; Marchetti, M.; Taddei, M. J. Comb. Chem. 2003, 5, 198.
17. Discover microwave ovens for organic synthesis are produced by the CEM Corporation. A photograph of the equipment is enclosed in the Supporting Information.
18. XANTPHOS: 9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene. Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3081. The ligand is commercially available from Sigma-Aldrich, Stream, and other chemical suppliers.
19. Leadbeater, N. E.; Torenius, H. M. J. Org. Chem. 2002, 67, 3145.
20. Scale applied to alkene 9. For security reasons, we did not fill the vial. However, the speed of the reaction allowed us to repeat the process 4 times, producing 4.8 g of aldehyde 10 in 30 min.
21. Marchetti, M.; Botteghi, C.; Paganelli, S.; Taddei, M. Adv. Synth. Catal. 2003, 345, 1229.
22. A similar behavior has already been observed under standard hydroformylation conditions. Ojima, I.; Tzamarioudaki, M.; Eguchi, M. J. Org. Chem. 1995, 60, 7078.