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. 2020 Mar 23;59(13):5242-5247.
doi: 10.1002/anie.201916471. Epub 2020 Feb 20.

Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates

Hai-Jun Tang  1 , Xinggui Zhang  1 , Yu-Feng Zhang  1 , Chao Feng  1
Affiliations

Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates

Hai-Jun Tang et al. Angew Chem Int Ed Engl. .

Abstract

A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.

Keywords: allenoates; arylation; fluorination; gold; redox catalysis.

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