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Ligand-Controlled α- and β-Arylation of Acyclic N-Boc Amines

Authors


  • Computational work performed by Dr. P. Larini. We thank the Agence Nationale de la Recherche (programme blanc “EnolFun”) and Institut Universitaire de France for financial support of this work. We also thank Prof. B. Andrioletti and L. Sandjong-Kuigwa for free access to and assistance with in situ IR instrument and Dr. E. Clot for fruitful discussions and comments.

Abstract

The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling.

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