1407999-33-0Relevant articles and documents
Radical amination of C(sp3)-H bonds using N -hydroxyphthalimide and dialkyl azodicarboxylate
Amaoka, Yuuki,Kamijo, Shin,Hoshikawa, Tamaki,Inoue, Masayuki
, p. 9959 - 9969 (2012)
A direct conversion of C(sp3)-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.