4.6 Article

Nickel-Catalyzed Direct Carboxylation of Olefins with CO2: One-Pot Synthesis of α,β-Unsaturated Carboxylic Acid Salts

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 51, Pages 16858-16862

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405528

Keywords

carbon dioxide; catalysis; C-C coupling reactions; metallacycles; nickel

Funding

  1. Heidelberg University
  2. state of Baden-Wurttemberg
  3. BASF SE
  4. Bundesministerium fur Bildung und Forschung (BMBF) [01RC1015A]

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The nickel-catalyzed direct carboxylation of alkenes with the cheap and abundantly available C-1 building block carbon dioxide (CO2) in the presence of a base has been achieved. The one-pot reaction allows for the direct and selective synthesis of a wide range of alpha,beta-unsaturated carboxylates (TON>100, TOF up to 6 h(-1), TON=turnover number, TOF=turnover frequency). Thus, it is possible, in one step, to synthesize sodium acrylate from ethylene, CO2, and a sodium salt. Acrylates are industrially important products, the synthesis of which has hitherto required multiple steps.

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