4.8 Article

Scandium-Catalyzed para-Selective Alkylation of Aromatic Amines with Alkenes

Journal

ORGANIC LETTERS
Volume 21, Issue 22, Pages 9055-9059

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03451

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Funding

  1. National Natural Science Foundation of China [21871204]
  2. 1000-Youth Talents Plan
  3. PAPD
  4. project of scientific and technologic infrastructure of Suzhou [SZS201708]

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An efficient para-alkylation of primary and secondary anilines with a variety of sterically encumbered alkenes using a simple beta-diketiminato scandium catalyst is reported. This protocol features 100% atom economy, excellent chemo- and regioselectivity, broad substrate scope, and good functional group tolerance. Mechanistic studies disclosed that the reaction probably proceeded via a tandem hydroamination/Hofmann-Martius rearrangement.

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