Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO2

doi:10.1016/S1872-2067(23)64468-7

Abstract

Abstract:

Photocatalytic carboxylation with CO₂ is a powerful strategy for the synthesis of functionalized carboxylic acids and their derivatives under mild conditions. However, the dicarboxylation of alkenes with CO₂ is still underdeveloped and confined to the formation of only two C-C bonds. Herein, we report the 1,3-dicarboxylation of unactivated alkenes with CO₂ via 1,2-aryl migration, which involves the cleavage of one C-C bond and the formation of three C-C bonds. This visible-light photocatalytic protocol is also distinguished by good functional group tolerance, broad substrate scope, and facile derivations of products to heterocyclic scaffolds. Mechanistic studies indicate that the in situ generated formate could act as the radical precursor of CO₂˙ˉ, and the following radical addition, 1,2-aryl migration, single electron reduction, and nucleophilic attack at the second CO₂ would afford the dicarboxylic acids.

Key words: Carbon dioxide, Visible-light photocatalysis, 1,3-Dicarboxylation, Unactivated alkene, 1,2-Aryl migration

Han-Zhi Xiao, Bo Yu, Si-Shun Yan, Wei Zhang, Xi-Xi Li, Ying Bao, Shu-Ping Luo, Jian-Heng Ye, Da-Gang Yu. Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO₂[J]. Chinese Journal of Catalysis, 2023, 50: 222-228.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64468-7

https://www.cjcatal.com/EN/Y2023/V50/I7/222

Figures/Tables 7

Fig. 1. State-of-the-art of visible light-driven dicarboxylations of alkenes with CO2.

Table 1 Optimization of reaction conditions a.

Table 2 Test of different substituents on the allylic position. a

Table 3 Scope of α,α-diaryl allylic amides.a

Scheme 1. Facile transformations of 2a.

Scheme 2. Mechanistic investigations.

Scheme 3. Plausible reaction mechanism.

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Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO₂

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