4.8 Article

Condensed-Phase, Halogen-Bonded CF3I and C2F5I Adducts for Perfluoroalkylation Reactions

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 12, Pages 3712-3716

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410954

Keywords

arenes; C-H functionalization; halogen bonding; pentafluoroethylation; trifluoromethylation

Funding

  1. European Community
  2. NSF [CHE-0952753]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [0952753] Funding Source: National Science Foundation

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A family of practical, liquid trifluoromethylation and pentafluoroethylation reagents is described. We show how halogen bonding can be used to obtain easily handled liquid reagents from gaseous CF3I and CF3CF2I. The synthetic utility of the new reagents is exemplified by a novel direct arene trifluoromethylation reaction as well as adaptations of other perfluoroalkylation reactions.

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