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Issue 6, 2021
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Photo-induced energy transfer relay of N-heterocyclic carbene catalysis: an asymmetric α-fluorination/isomerization cascade

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Abstract

The geometric configuration of olefin products is often driven by thermodynamic control in synthesis. Methods enabling switching of cis/trans selectivity are rare. Recently, photosensitized approaches have emerged as a powerful tool for accomplishing this task. In this report, we report an in situ isomerization of an N-heterocyclic carbene (NHC)-bound intermediate by a photo-induced energy transfer process that leads to selective access of chiral allylic fluorides with a cis-olefin geometry. In the absence of a photocatalyst or light, the reaction proceeds smoothly to give (E)-olefin products, while the (Z)-isomer can be obtained under photosensitizing conditions. Preliminary mechanistic experiments suggest that an energy transfer process might be operative.

Graphical abstract: Photo-induced energy transfer relay of N-heterocyclic carbene catalysis: an asymmetric α-fluorination/isomerization cascade

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Supplementary files

Article information


Submitted
03 Nov 2020
Accepted
11 Dec 2020
First published
12 Dec 2020

Chem. Commun., 2021,57, 729-732
Article type
Communication

Photo-induced energy transfer relay of N-heterocyclic carbene catalysis: an asymmetric α-fluorination/isomerization cascade

X. Jiang, E. Li, J. Chen and Y. Huang, Chem. Commun., 2021, 57, 729
DOI: 10.1039/D0CC07264H

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