4.7 Article

Stereoselective defluorinative carboxylation of gem-difluoroalkenes with carbon dioxide

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 21, Pages 3678-3682

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9qo00923j

Keywords

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Funding

  1. 973 Program [2015CB856600]
  2. NSFC [21871090, 21573073]
  3. Program of Shanghai Academic/Technology Research Leader [18XD1401500]
  4. Fundamental Research Funds for the Central Universities

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We report the copper-catalyzed defluorinative carboxylation of gem-difluoroalkenes with CO2. Using cheap and easily available CuI as the catalyst and bis(pinacolatodiboron) as the stoichiometric reductant, the reaction efficiently converts the alkenyl C-F bond to a carboxyl group with complete retention of stereochemistry, thus providing fluoroalkenyl carboxylic acids in good to excellent yields.

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