Using CO2 to Make Carboxylic Acids

  • Author: ChemistryViews.org
  • Published: 23 June 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Journal of Organic Chemistry/ACS Publications
thumbnail image: Using CO<sub>2</sub> to Make Carboxylic Acids

Carbon dioxide is a sustainable chemical feedstock and can be incorporated into organic molecules to form carboxylic acids and their derivatives. Unsaturated carboxylic acids are particularly useful for further functionalization.


Tianning Diao, New York University, USA, and colleagues have developed a nickel-catalyzed coupling of CO2 to enynes that gives α,β-unsaturated carboxylic acids (example product pictured). The team used 1,6- or 1,7-enynes as substrates, a nickel 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene complex as the catalyst, and diethylzinc as a reductant under 1 atm CO2 pressure to synthesize the unsaturated carboxylic acids.


The reaction selectively gives Z-olefins and tolerates heteroatoms, which allows the synthesis of, e.g., pyrrolidine and furan derivatives. When terminal 1,7-enynes or alkenes with large substituents are used as substrates, the regioselectivity of the reaction changes and the products are unconjugated carboxylic acids. The researchers propose a hydride insertion mechanism for the reaction, which stands in contrast to a transmetalation mechanisms involved in previous reactions that incorporate CO2 into organic compounds.


 

Article Views: 717

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH