4.7 Article

Iridium-Catalyzed Selective Synthesis of 4-Substituted Benzofurans and Indoles via Directed Cyclodehydration

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 17, Pages 2850-2854

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900570

Keywords

C-C bond formation; C-H functionalization; heterocycles; homogeneous catalysis; iridium

Funding

  1. Wasedn University Grant for Special Research
  2. Promotion of Science (JSPS)

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A directed cyclization-dehydration cascade of alpha-aryloxy ketones and alpha-arylamino ketones was efficiently catalyzed by a cationic iridium-BINAP complex, which afforded various types of 4-substituted benzofurans and indoles in high yields with complete regioselectivity. The newly developed protocol also enabled the enantioselective preparation of chiral 4-acetyloxindole using a chiral iridium catalyst.

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