Direct access to ketones from aldehydes via rhodium-catalyzed cross-coupling reaction with potassium trifluoro(organo)borates

Journal of the American Chemical Society

Volumn 126, Issue 47, 2004, Pages 15356-15357

  Pucheault, Mathieu ^a   Darses, Sylvain ^a   Genet, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; KETONE DERIVATIVE; POTASSIUM; RHODIUM;

ADDITION REACTION; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CROSS COUPLING REACTION; HECK REACTION; PHASE TRANSITION; PROTON TRANSPORT;

EID: 9644295537     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044749b     Document Type: Article

References (40)

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21. For some examples, see: (a) Oi, S.; Moro, M.; Inoue, Y. Chem. Commun. 1997, 1621. (b) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (c) Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683. (d) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (e) Li, C.-J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538. (f) Fürstner, A.; Krause, H. Adv. Synth. Catal. 2001, 4, 343. (g) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001. 123, 7451.
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24. Direct formation of ketone via such reaction has been observed as a byproduct (Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298) or via an isomerization mechanism in the reaction with alkenylboronic acids (Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett. 2002, 1733).
25. Direct formation of ketone via such reaction has been observed as a byproduct (Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298) or via an isomerization mechanism in the reaction with alkenylboronic acids (Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett. 2002, 1733).
26. During the preparation of this manuscript, Zou et al. reported direct coupling of cinnamaldehydes with arylboronic acids under Rh catalysis with concomitant C=C reduction: Wang, Z.; Zou, G.; Tang, J. Chem. Commun. 2004, 1192.
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34. 3 has proven to be highly suited in rhodium-catalyzed 1,2-additions of boronic acids to aldehydes: see ref 8d.
35. Hartwig et al. reported that the reaction between isolated arylrhodium(I) complexes and aldehydes resulted in the formation of ketone upon heating at 80 °C via the intermediate formation of a rhodium alkoxide complexes, see: Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1674. Krug, C.; Hartwig, J. F. Organometallics 2004, 23, 4594.
36. Hartwig et al. reported that the reaction between isolated arylrhodium(I) complexes and aldehydes resulted in the formation of ketone upon heating at 80 °C via the intermediate formation of a rhodium alkoxide complexes, see: Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1674. Krug, C.; Hartwig, J. F. Organometallics 2004, 23, 4594.
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