Chemistry Letters, Vol.42, No.7, 691-693, 2013
Synthesis of alpha-Arylcarboxylic Acid Amides from Silyl Enol Ether via Migratory Amidation with 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate
alpha-Arylcarboxylic acid amides were synthesized by reacting silyl enol ethers of aryl ketones and 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP, 1). Silyl enol ethers react with ADMP 1 to give N-(alpha-arylacyl)guanidines via the migration of aryl groups in enol ethers. The products were transformed to the corresponding alpha-aryl acetamides by treating with LiAlH4.