Kitamura Mitsuru, Ohtsuka Kazuki, Eto Takashi, Tsuzaki Masato, Wada Mayuko, Shimooka Hirokazu, Okauchi Tatsuo
Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensuicho, Tobata, Kitakyushu 804-8550, Japan.
J Org Chem. 2023 Nov 3;88(21):15494-15500. doi: 10.1021/acs.joc.3c01743. Epub 2023 Oct 24.
The diazo-transfer reaction of nonactivated ketone under mild reaction conditions was developed. Various nonactivated ketones such as aryl methyl ketones, -alkyl methyl ketones, and cyclic ketones were transformed into their corresponding α-diazoketones in one step by treating 2-azido-1,3-bis(2,6-diisopropylphenyl)imidazolium hexafluorophosphate (IPrAP) in the presence of PrNH in ethylene glycol. In the reaction of IPrAP with -alkyl methyl ketone and -alkyl aryl ketones, migratory amidation proceeded under the reaction conditions to afford the corresponding amides.
