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. 2016 Jul 25;55(31):9084-7.
doi: 10.1002/anie.201604268. Epub 2016 Jun 8.

Catalytic C(sp(3) )-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ

Yan Xu  1 , Michael C Young  1 , Chengpeng Wang  1 , David M Magness  1 , Guangbin Dong  2
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Catalytic C(sp(3) )-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ

Yan Xu et al. Angew Chem Int Ed Engl. .

Abstract

Herein, we report the palladium-catalyzed direct arylation of unactivated aliphatic C-H bonds in free primary amines. This method takes advantage of an exo-imine-type directing group (DG) that can be generated and removed in situ. A range of unprotected aliphatic amines are suitable substrates, undergoing site-selective arylation at the γ-position. Methyl as well as cyclic and acyclic methylene groups can be activated. Furthermore, when aniline-derived substrates were used, preliminary success with δ-C-H arylation was achieved. The feasibility of using the DG component in a catalytic fashion was also demonstrated.

Keywords: C−H activation; arylation; directing groups; palladium catalysis; primary amines.

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