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β-Amination of Aliphatic Amides via the β-C(sp3)—H Bonds Activation

Yu et al. have reported the β-amination of aliphatic amides via β-C(sp3)—H bonds activation. According to their results, the β-C(sp3)—H bonds activation of amides has been achieved by using a catalytic system of a [Pd(allyl)Cl]2 complex and a tris[3,5-bis(trifluoromethyl)phenyl]phosphine ligand in combination with N-perfluorophenyl aliphatic amides directly coordinated with the palladium catalysts. In this reaction, aliphatic amides with a methyl group and other alkyl groups at the α-position are required for proceeding with the amination wherein the C(sp3)—H bond of the methyl group is selectively cleaved. Also, O-benzoyl hydroxylamines modified with an amino group of cyclic aliphatic amines such as morpholines and piperazines are used as aminating reagents, and the given products after the aminations are useful for the synthetic intermediates of bioactive compounds. Especially, when using a piperidone derivative as an aminating reagent, the synthetic product 6 can be converted to the β-amino acid by removing the piperidone unit.

A1479,C2160,T2526

References

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