Efficient Trifluoromethylation of Alkenes

  • Author: ChemistryViews
  • Published: 27 September 2011
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Journal of the American Chemical Society/ACS Publications
thumbnail image: Efficient Trifluoromethylation of Alkenes

Molecules bearing trifluoromethyl groups have been widely applied in the fields of functional materials, agrochemicals, and pharmaceuticals due to their hydrophobicity, metabolic stability, and bioavailability.


Jianbo Wang and colleagues, Peking University, China, report a route to synthesize allylic trifluoromethylated compounds under mild conditions. The reaction employs cheap copper chloride as the catalyst and a hypervalent iodine(III) reagent (pictured) as both the oxidant and the CF3 source. The hypervalent iodide reagent is easily accessible from commercially available 2-iodobenzoic acid and provided the desired products in up to 97 % isolated yield. Simple alkenes can be used as substrates and the reaction tolerates a wide range of functional groups.

This methodology represents a rare example of a general and highly efficient direct trifluoromethylation of terminal olefins.


Article Views: 3448

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