4.8 Article

F- Nucleophilic-Addition-Induced [3+2] Annulation: Direct Access to CF3-Substituted Indenes

Journal

ORGANIC LETTERS
Volume 20, Issue 17, Pages 5190-5193

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02128

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Funding

  1. Thousand Talents Plan Youth Program
  2. Jiangsu Specially-Appointed Professor Plan
  3. Natural Science Foundation of Jiangsu Province [BK20170984]
  4. SICAM Fellowship by the Jiangsu National Synergetic Innovation Center for Advanced Materials

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An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same step, which delicately joins together these two different metallic intermediates. molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.

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