Benzylamine ortho-arylation by using C-H activation methodology

CHED 354

Olafs Daugulis and Anna Lazareva. Department of Chemistry, University of Houston, 136 Fleming Building, Houston, TX 77204
The focus of this research is the development of new and useful transformations based on carbon-hydrogen bond activation by transition metal complexes. A method previously developed in our group was applied to the arylation of benzylamines after modification of reaction conditions. ortho-Arylation was successful for a variety of substituted and unsubstituted benzylamines. Surprisingly, the method is useful also for ortho-arylation of N-H containing benzylamines. This method is very tolerant with respect to functional groups on both the amine moiety and aryl iodide. We are extending the arylation methodology to functionalization of sp3 C-H bonds. Aliphatic methyl groups of unprotected amines can be arylated under standard reaction conditions.