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Pd(II)-catalyzed γ-C(sp 3 )-H arylation of primary amines is realized by using 2-hydroxynicotinaldehyde as a catalytic transient directing group. Importantly, the catalyst and the directing group loading can be lowered to 2% and 4% respectively, thus demonstrating high efficiency of this newly designed transient directing group. Heterocyclic aryl iodides are also compatible with this reaction. Furthermore, swift synthesis of 1,2,3,4-tetrahydronaphthyridine derivatives is accomplished using this reaction.

Pd-Catalyzed γ-C(sp3)–H Arylation of Free Amines Using a Transient Directing Group

Pd-Catalyzed γ-C(sp³)–H Arylation of Free Amines Using a Transient Directing Group