Alkylation of aldehydes with trialkylboranes in water

Advanced Synthesis and Catalysis

Volumn 348, Issue 12-13, 2006, Pages 1543-1546

  Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aldehydes; Alkylation; Cyclodextrin; Nickel; Trialkylboranes; Water

Indexed keywords

EID: 33748254922     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606136     Document Type: Article

References (35)

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19. for boron: g) M. Sugiura, K. Hirano, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7182-7183.
20. For rhodium: a) M. Ueda, N. Miyaura, J. Org. Chem. 2000, 65, 4450-4452;
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24. The only precedent: C. C. K. Keh, C. Wei, C.-J. Li, J. Am. Chem. Soc. 2003, 125, 4062-4063.
25. Recently, Woodward has reported alkylation of aldehydes with air-stable trialkylaluminum reagents in organic solvent under nickel catalysis: K. Biswas, O. Prieto, P. J. Goldsmith, S. Woodward, Angew. Chem. Int. Ed. 2005, 44, 2232-2234.
26. K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2005, 7, 4689-4691.
27. 3P were ineffective.
28. [8]
29. 2-Coordinated nickel complexes with aldehydes have been reported, see: a) S. Ogoshi, M. Oka, H. Kurosawa, J. Am. Chem. Soc. 2004, 126, 11802-11803.
30. [7, 8] and b) K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2006, 8, 483-485.
31. -1, respectively. α-CD is known to accommodate a phenyl ring most tightly, see: F. Hapiot, S. Tilloy, E. Monflier, Chem. Rev. 2006, 106, 767-781.
32. We assumed that the substitution at the meta-position in 6g would allow α-CD to dissociate easily from the phenyl ring of 6g due to the steric factors.
33. In the catalytic cycle, transmetalation of the nickel complex 10 with trialkylborane would be a key step. Therefore, we suppose that in the reaction with trialkylborane 6f, interactions between the oxygen atom of 6f and the nickel or boron center would suppress the step to result in the low yield (Table 2, entry 6). On the basis of the assumption, we thus tested the addition of cyclodextrins to the reaction media. Namely, we expected that the internal cavity of cyclodextrins would accommodate the aromatic ring of 6f to block out the unfavorable interaction as described above.
34. Cyclodextrin can interact with phosphine or nickel(phosphine)complex to improve the catalytic activity: a) E. Monflier, H. Bricout, F. Hapiot, S. Tilloy, A. Aghmiz, A. M. Masdeu-Bultó, Adv. Synth. Catal. 2004, 346, 425-431;
35. b) C. Binkowski, J. Cabou, H. Bricout, F. Hapiot, E. Monflier, J. Mol. Catal. A 2004, 215, 23-32.