Photocatalyzed Direct α‐Alkylation of Esters Using Styrenes

A mild photocatalyzed approach to achieve the α‐alkylation of esters via formation of an α ‐radical is disclosed here. Cesium enolates of esters were generated in situ using Cs2CO3 as a base. A subsequent photocatalyzed oxidation at the α‐carbon of these enolates produced an α‐radical that was added...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-07, Vol.365 (14), p.2361-2366
Main Authors: Wang, Pengzhi, Bay, Anna V., Farnam, Emelia J., Scheidt, Karl A.
Format: Article
Language:English
Subjects:
Activated carbon
Alkylation
Carbonyl compounds
Cesium
Cesium enolates
Esters
Oxidation
Photoredox catalysis
Styrenes
α-Alkylation
α-Radical
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Summary:A mild photocatalyzed approach to achieve the α‐alkylation of esters via formation of an α ‐radical is disclosed here. Cesium enolates of esters were generated in situ using Cs2CO3 as a base. A subsequent photocatalyzed oxidation at the α‐carbon of these enolates produced an α‐radical that was added into activated alkenes. This is the first example accessing the α‐carbon radical of esters in photoredox catalyed transformations.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300253