4.8 Article

Palladium-Catalyzed Enantioselective Narasaka-Heck Reaction/Direct C-H Alkylation of Arenes: Iminoarylation of Alkenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 32, Pages 9577-9581

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705641

Keywords

asymmetric catalysis; C-H activation; dihydropyrroles; domino reactions; Narasaka-Heck reactions

Funding

  1. EPFL (Switzerland)
  2. Swiss National Science Foundation (SNSF)

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A palladium-catalyzed reaction of gamma,delta-unsaturated oxime esters with oxadiazoles afforded dihydropyrroles in good to excellent yields through an intramolecular iminopalladation/intermolecular direct heteroarene C-H alkylation cascade. This unprecedented iminoarylation of alkenes was subsequently realized in an enantioselective manner in the presence of a chiral bidentate phosphine ligand (Synphos).

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