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Updated: Mar 19, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Catalytic C(sp(3) )-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ
Yan Xu1, Michael C Young1, Chengpeng Wang1
1Department of Chemistry, University of Texas at Austin, Austin, TX, 78712, USA.
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.
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