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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 8
BKCSDE 27(8)
August 20, 2006 

Oxidation of Aromatic Aldehydes with Tetrabutylammonium Fluoride:Competition with the Cannizzaro Reaction
Kyoo-Hyun Chung*, Byung-Chul Moon, Choong Hwan Lim, Jin Pil Kim, Jae Hak Lee, Dae Yoon Chi*
Oxidation, Tetrabutylammonium fluoride, Nucleophilicity of hydride, Cannizzaro reaction, Aromatic aldehyde
During the synthesis of 4-fluorobenzaldehyde via the SNAr reaction of 4-nitrobenzaldehyde with TBAF, it was found that an equivalent amount of TBAF could oxidize benzaldehyde to benzoic acid. The reaction of 4-nitrobenzaldehyde with tetrabutylammonium fluoride (TBAF) gave 4-nitrobenzoic acid in high yield. Depending on the reaction conditions, other aromatic aldehydes produced acids with fewer amounts of alcohols. However, this type of oxidation has limited practical applications. Nevertheless, the mechanism is quite different from the Cannizzaro reaction because the amounts of the acid salt and alcohol formed were different.
1203 - 1205
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