Meta-Olefination of Fluoroarenes

  • Author:
  • Published: 02 April 2020
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Chemical Science/Royal Society of Chemistry
  • Associated Societies: Royal Society of Chemistry (RSC), UK
thumbnail image: <i>Meta</i>-Olefination of Fluoroarenes

Aryl olefins are useful intermediates and products in organic synthesis. There is a variety of methods for the ortho-olefination of arenes, but few approaches for the meta-selective olefination. Existing methods for the meta-selective reaction require directing groups that cannot be installed on fluoro-substituted arenes. However, fluoroarenes are common, e.g., in pharmaceutical chemistry.

Igor Larrosa and colleagues, University of Manchester, UK, have developed a meta-selective olefination of fluoroarenes that uses CO2 as a traceless, easy-to-install directing group. The olefination can be performed in a one-pot process. The team first used a lithiation/carboxylation protocol with sec-butyllithium and gaseous CO2 to install the carboxylate directing group at the ortho-position. The olefination was then performed with a range of alkynes, using [Ru(C6Me6)(OAc)2] as a catalyst and 1,2-dichloroethane (DCE) as the solvent.

The desired products were obtained in good to excellent yields and with complete meta-regioselectivity. According to the researchers, this is the first example of a method for the meta-selective olefination of fluoroarenes.



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