Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 31, Pages 9084-9087Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604268
Keywords
arylation; C-H activation; directing groups; palladium catalysis; primary amines
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Funding
- Frasche Foundation
- ACS PRF
- Welch Foundation [F-1781]
- NSF [CHE-1254935]
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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 g-position. Methyl as well as cyclic and acyclic methylene groups can be activated. Furthermore, when aniline-derived substrates were used, preliminary success with delta-C-H arylation was achieved. The feasibility of using the DG component in a catalytic fashion was also demonstrated.
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