4.8 Article

Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 49, Pages 14866-14870

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506581

Keywords

acetanilides; branch selectivity; hydroarylation; iridium; phosphine ligands

Funding

  1. Bristol Chemical Synthesis CDT (EPSRC) [EP/G036764/1]
  2. EPSRC [EP/K03927X/1] Funding Source: UKRI
  3. Engineering and Physical Sciences Research Council [1379027, EP/K03927X/1] Funding Source: researchfish

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An iridium(I) catalyst system, modified with the wide-bite-angle and electron-deficient bisphosphine d(F)ppb (1,4-bis(di(pentafluorophenyl)phosphino)butane) promotes highly branch-selective hydroarylation reactions between diverse acetanilides and aryl-or alkyl-substituted alkenes. This provides direct and ortho-selective access to synthetically challenging anilines, and addresses long-standing issues associated with related Friedel-Crafts alkylations.

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