4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 10, Pages 2678-2682

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310904

Keywords

arylation; CC coupling; cross-coupling; density functional calculations; palladium

Funding

  1. Agence Nationale de la Recherche
  2. Institut Universitaire de France

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

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