Nickel-catalyzed direct carboxylation of olefins with CO2

One-pot synthesis of α,β-unsaturated carboxylic acid salts

Nfflria Huguet, Ivana Jevtovikj, Alvaro Gordillo, Michael L. Lejkowski, Ronald Lindner, Miriam Bru, Andrey Y. Khalimon, Frank Rominger, Stephan A. Schunk, Peter Hofmann, Michael Limbach

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

The nickel-catalyzed direct carboxylation of alkenes with the cheap and abundantly available C1 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 a,b-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.

Original languageEnglish
Pages (from-to)16858-16862
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number51
DOIs
Publication statusPublished - Dec 15 2014
Externally publishedYes

Fingerprint

Carboxylation
Alkenes
Carboxylic Acids
Nickel
Carboxylic acids
Olefins
Salts
Sodium
Acrylates
Carbon Dioxide
Carbon dioxide
Ethylene
ethylene
acrylic acid

Keywords

  • C-C coupling reactions
  • Carbon dioxide
  • Catalysis
  • Metallacycles
  • Nickel

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Huguet, N., Jevtovikj, I., Gordillo, A., Lejkowski, M. L., Lindner, R., Bru, M., ... Limbach, M. (2014). Nickel-catalyzed direct carboxylation of olefins with CO2: One-pot synthesis of α,β-unsaturated carboxylic acid salts. Chemistry - A European Journal, 20(51), 16858-16862. https://doi.org/10.1002/chem.201405528

Nickel-catalyzed direct carboxylation of olefins with CO2 : One-pot synthesis of α,β-unsaturated carboxylic acid salts. / Huguet, Nfflria; Jevtovikj, Ivana; Gordillo, Alvaro; Lejkowski, Michael L.; Lindner, Ronald; Bru, Miriam; Khalimon, Andrey Y.; Rominger, Frank; Schunk, Stephan A.; Hofmann, Peter; Limbach, Michael.

In: Chemistry - A European Journal, Vol. 20, No. 51, 15.12.2014, p. 16858-16862.

Research output: Contribution to journalArticle

Huguet, N, Jevtovikj, I, Gordillo, A, Lejkowski, ML, Lindner, R, Bru, M, Khalimon, AY, Rominger, F, Schunk, SA, Hofmann, P & Limbach, M 2014, 'Nickel-catalyzed direct carboxylation of olefins with CO2: One-pot synthesis of α,β-unsaturated carboxylic acid salts', Chemistry - A European Journal, vol. 20, no. 51, pp. 16858-16862. https://doi.org/10.1002/chem.201405528
Huguet, Nfflria ; Jevtovikj, Ivana ; Gordillo, Alvaro ; Lejkowski, Michael L. ; Lindner, Ronald ; Bru, Miriam ; Khalimon, Andrey Y. ; Rominger, Frank ; Schunk, Stephan A. ; Hofmann, Peter ; Limbach, Michael. / Nickel-catalyzed direct carboxylation of olefins with CO2 : One-pot synthesis of α,β-unsaturated carboxylic acid salts. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 51. pp. 16858-16862.
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