Cyano-Functionalized Fluoroalkylated Alkenes Made in One Step

  • Author: ChemistryViews.org
  • Published: 27 August 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Cyano-Functionalized Fluoroalkylated Alkenes Made in One Step

Organofluorine compounds are often useful, e.g., in medicinal chemistry. There are several methods to synthesize aromatic compounds with fluoroalkyl substituents, while paths to fluoroalkylated alkenes are less well studied. The available methods generally only introduce the fluoroalkyl group into the alkene. Combining this transformation with the introduction of a second useful functional group could be a step-economic way to synthesize complex organic molecules.


Hongli Bao, University of the Chinese Academy of Sciences, Fujian and Beijing, and colleagues have developed a copper-catalyzed radical cyanoperfluoroalkylation of alkynes to give doubly functionalized alkenes (pictured). The team used a three-component reaction between alkynes, perfluoroalkyl iodides, and trimethylsilyl cyanide. The reaction was catalyzed by Cu(CH3CN)4BF4, together with 2,2':6',2''-terpyridine as a ligand and lauroyl peroxide (LPO) as a radical initiator.


The desired products were obtained in generally good yields and the reaction has good functional group tolerance. The cyano group can be further transformed into other functional groups, which makes the reaction's products useful intermediates for organic synthesis.


 

Article Views: 578

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