Science of Synthesis

Schall, A.; Reiser, O., Science of Synthesis, (2007) 25, 622.

The activation of simple formamides by Lewis acids results in intermediates that display too low electrophilicity to be useful as formylating agents.[‌84‌] However, the reactivity increases when electron-withdrawing acyl groups are placed on the amide nitrogen in addition to using a Lewis acid. Because mixed substituted formamides bear the danger of producing side products due to nonselective acyl transfer, only di- and triformamides initially appeared to be suitable formylation reagents. More recently, tris(diformylamino)methane was introduced as a broadly applicable reagent for the synthesis of aromatic aldehydes by Lewis acid mediated formylation.

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References

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• 8.Meeeee-Meee, (8888) M 8, 88.