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

ABSTRACT: Pd(II)-catalyzed ?-C(sp3)-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.

SUBMITTER: Wu Y 

PROVIDER: S-EPMC5535771 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Pd-Catalyzed γ-C(sp<sup>3</sup>)-H Arylation of Free Amines Using a Transient Directing Group.

Wu Yongwei Y   Chen Yan-Qiao YQ   Liu Tao T   Eastgate Martin D MD   Yu Jin-Quan JQ  

Journal of the American Chemical Society 20161101 44

Pd(II)-catalyzed γ-C(sp<sup>3</sup>)-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 us  ...[more]

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