duff formylation -- alternative acids?
With acetic acid, the Duff reaction works only on phenols and anilines. But with trifluoroacetic acid, the reaction scope is much broader, and even
toluene can be formylated.
What I wonder is if other acids could work? The first thing that comes to mind is oxalic acid, which has acidity closer to trifluoroacetic acid but
still reacts like a carboxylic acid in many situations. Pyroglutamic acid, lactic acid or pyruvic acid might also be effective. Sulfonic acids were
not so good IIRC. In this paper a mixture of acetic and trifluoroacetic acids was used for the formylation of 1,4-diethoxybenzene and
4-(4'-phenoxyphenoxy)-benzene:
https://www.arkat-usa.org/get-file/19827/
Attachment: smith1972.pdf (241kB)
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[Edited on 14-3-2020 by clearly_not_atara]
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