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Synfacts 2025; 21(01): 52
DOI: 10.1055/a-2467-4990
Metals in Synthesis

Photoredox-Catalyzed Direct Olefination of Carboxylic Acids with Phenyl Vinyl Ketones

Contributor(s):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Dáiríne M. Morgan 
Zeng H, Yin R, Zhao Y *, Ma J-A *, Wu J *. Tianjin University, P. R. China and National University of Singapore, Republic of Singapore
Modular Alkene Synthesis from Carboxylic Acids, Alcohols and Alkanes via Integrated Photocatalysis.

Nat. Chem. 2024;
16: 1822-1830
DOI: 10.1038/s41557-024-01642-6
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Keywords

alkenes - carboxylic acids - Giese reaction - olefination - photoredox catalysis - Norrish fragmentation

Significance

An iridium-photoredox-catalyzed protocol for the direct conversion of carboxylic acids into olefins using phenyl vinyl ketones as olefination reagents is reported. This approach makes use of an initial Giese-type addition of the photochemically generated alkyl radical, followed by a Norrish-type II fragmentation to generate the desired olefin.


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Comment

By modification of the reaction conditions, this method can also be applied to the olefination of alkanes and alcohols, making it possible to functionalize each of these groups selectively. The synthetic utility of the reaction is further demonstrated through scale-up and the synthesis of natural products via shorter routes than previously reported.


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Publication History

Article published online:
20 December 2024

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