Greener Synthesis of Amides

  • Author:
  • Published: 08 July 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Greener Synthesis of Amides

Amide bonds are important, e.g., in biological systems, drugs, agrochemicals, and polymers. Usually, amides are synthesized by coupling amines with activated carboxylic acid derivatives. However, the reactants used to activate carboxylic acids are often toxic and can usually not be recovered and reused.

Bert U. W. Maes, University of Antwerp, Belgium, and colleagues have developed a greener approach to the synthesis of amides. The team used readily accessible S-phenyl thiocarbamate derivatives (pictured left) as starting materials and coupled them with Grignard reagents in 2-methyl-tetrahydrofuran at room temperature. An oxidative workup using an aqueous ammonium hydroxide solution under an oxygen atmosphere then gave the desired secondary amides (pictured right) and diphenyl disulfide (PhSSPh).

The diphenyl disulfide product can be oxidized to S-phenyl benzenethiosulfonate, which can then be reused to synthesize thiocarbamates as the starting materials for further amide syntheses. According to the researchers, the method can be used for the preparation of amides which are not accessible via other approaches and the recovery of the thiophenolate leaving group as diphenyl disulfide lowers waste production.



Article Views: 1768

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

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

Follow on Facebook Follow on Twitter Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH