Visible‐Light‐Assisted Gold‐Catalyzed Fluoroarylation of Allenoates

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 mil...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-03, Vol.59 (13), p.5242-5247
Main Authors: Tang, Hai‐Jun, Zhang, Xinggui, Zhang, Yu‐Feng, Feng, Chao
Format: Article
Language:English
Subjects:
Allene
allenoates
Aromatic compounds
arylation
Catalysis
Fluorides
fluorination
Fluorine
Functional groups
Gold
Hydrogen fluoride
redox catalysis
Stereoselectivity
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Summary: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. Leading light: A regio‐ and stereoselective fluoroarylation of allenic esters through visible‐light‐promoted gold redox catalysis with cost‐effective Et3N⋅3 HF as the nucleophilic fluorine source is reported. Preliminary mechanistic studies reveal concomitant activation of the allene motif by a high‐valent gold complex and the hydrogen fluoride by hydrogen bonding with the ester group, thereby enabling the otherwise challenging fluorine incorporation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201916471