Vitamin Derivative Acts as Photocatalyst

  • Author:
  • Published: 25 February 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Vitamin Derivative Acts as Photocatalyst

Nitriles are useful intermediates in organic synthesis. They can easily be converted into a variety of other functional groups. Nitriles can be synthesized via a decarboxylative cyanation of carboxylic acids. However, existing approaches for this reaction require multiple steps or expensive catalysts.

Jose C. Gonzalez-Gomez, Universidad de Alicante, Spain, and colleagues have developed a simple method for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. The method uses riboflavin tetraacetate as a low-cost, non-toxic photocatalyst, which can be prepared from riboflavin (vitamin B2) in a single step. Toluenesulfonyl cyanide (TsCN) was used as a cyanide source. The team was able to convert a range of carboxylic acids into the corresponding nitriles in moderate to good yields.

According to the researchers, the riboflavin tetraacetate promotes the oxidation of the carboxylic acid after activation with visible light, followed by a rapid decarboxylation of the generated acyloxyl radical, and trapping of the remaining alkyl radical with TSCN. The reaction tolerates a variety of functional groups.


Article Views: 916

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, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

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