Synlett 2024; 35(17): 1937-1946
DOI: 10.1055/s-0043-1763755
synpacts

Carboxylation of Alkenes with CO2 via Photocatalytic Cleavage of C=C Double Bonds

Pan-Feng Yuan
a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, No. 2, 1st North Street, Zhongguancun, Haidian District, Beijing 100190, P. R. of China
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a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, No. 2, 1st North Street, Zhongguancun, Haidian District, Beijing 100190, P. R. of China
b   University of Chinese Academy of Sciences, No. 80 Zhongguancun East Road, Haidian District, Beijing 100049, P. R. of China
› Author Affiliations
This work was financially supported by the National Natural Science Foundation of China (22271293), the CAS Project for Young Scientists in Basic Research (YSBR-050) and the Chinese Academy of Sciences.


Abstract

The cleavage of double bonds in alkenes constitutes an integral process in converting feedstock materials into high-value synthetic intermediates. Well-known examples such as the oxidative cleavage of olefins and olefin metathesis only facilitate the synthesis of oxygen-containing compounds and the recombination of olefins. Therefore, it is appealing to extend C=C double bond cleavage to yield more abundant transformations. Herein, we report a novel photocatalytic approach for the deconstructive carboxylation of alkenes with CO2 for the synthesis of carboxylic acids in the absence of transition metals. Compared with reported carboxylations with CO2 during which carbon numbers are typically increased, we achieve the exchange of carbon dioxide with one of the carbons of the alkene double bond, thus providing carboxylic acids with unchanged carbon numbers when terminal alkenes are used.



Publication History

Received: 04 March 2024

Accepted after revision: 29 April 2024

Article published online:
14 May 2024

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