Koji Hirano et al.
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knowledges JSPS for financial support.
[6] The only precedent: C. C. K. Keh, C. Wei, C.-J. Li, J.
Am. Chem. Soc. 2003, 125, 4062–4063.
[7] Recently, Woodward has reported alkylation of alde-
hydes with air-stable trialkylaluminum reagents in or-
ganic solvent under nickel catalysis: K. Biswas, O.
Prieto, P. J. Goldsmith, S. Woodward, Angew. Chem.
Int. Ed. 2005, 44, 2232–2234.
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[9] NiCl2 and Ni(acac)2 did not catalyze the reaction.
A
Other ligands such as Ph3P, n-Bu3P, and (c-C6H11)3P
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[10] Similar trends were observed in organic solvents, see
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[13] We assumed that the substitution at the meta-position
in 6g would allow a-CD to dissociate easily from the
phenyl ringof 6g due to the steric factors.
[14] 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 trial-
kylborane 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 ex-
pected that the internal cavity of cyclodextrins would
accommodate the aromatic ringof 6f to block out the
unfavorable interaction as described above.
[15] Cyclodextrin can interact with phosphine or nickel-
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ꢀ 2006 Wiley-VCH VerlagGmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2006, 348, 1543 – 1546