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Published on: June 21, 2017
Diazo-Transfer Reaction of Nonactivated Ketones with 2-Azido-1,3-bis(2,6-diisopropylphenyl)imidazolium
Mitsuru Kitamura1, Kazuki Ohtsuka1, Takashi Eto1
1Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensuicho, Tobata, Kitakyushu 804-8550, Japan.
Abstract:
The diazo-transfer reaction of nonactivated ketone under mild reaction conditions was developed. Various nonactivated ketones such as aryl methyl ketones, sec-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 Pr2NH in ethylene glycol. In the reaction of IPrAP with prim-alkyl methyl ketone and prim-alkyl aryl ketones, migratory amidation proceeded under the reaction conditions to afford the corresponding amides.
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