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Catalytic C(sp 3 )−H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ
Author(s) -
Xu Yan,
Young Michael C.,
Wang Chengpeng,
Magness David M.,
Dong Guangbin
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604268
Subject(s) - aniline , imine , chemistry , catalysis , primary (astronomy) , methylene , palladium , in situ , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , physics , astronomy
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.