Protic Solvent-Promoted Neutral Allylation of Aldehydes and Ketones with 1,8-Bis(allylstannyl)naphthalenes

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Abstract
The allylation reactions of carbonyl compounds using 1,8-bis(dibutylstannyl)naphthalene 1 (R = Bu) were dramatically promoted by using a mixture of THF and CF3CH2OH (5:1) as solvent. The rate acceleration was due to the enhancement of the Brønsted acidity of CF3CH2OH by the formation of the chelate complex 6 (R = CH2CF3) resulting from the chelation effect of two neighboring tin atoms.

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