Visible-light-driven alkene dicarboxylation with formate and CO<sub>2</sub> under mild conditions

Zhang, Fulin; Wu, Xiao-Yang; Gao, Pan-Pan; Zhang, Hao; Li, Zhu; Ai, Shangde; Li, Gang

doi:10.1039/d3sc04431a

Chem. Sci.

2024

DOI: 10.1039/d3sc04431a

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Visible-light-driven alkene dicarboxylation with formate and CO₂ under mild conditions

Fulin Zhang,

Xiao-Yang Wu,

Pan-Pan Gao

et al.

Abstract: The low-cost formate salt was used as the reductant and part of the carboxyl source in a visible-light-driven dicarboxylation of diverse alkenes, including simple styrenes. The highly competing hydrocarboxylation side...

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Cited by 11 publications

References 95 publications

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Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO₂

Kharlamova,

Averin,

Bondarenko

et al. 2024

Adv Synth Catal

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A visible light photoredox‐catalyzed bifunctionalization of styrenes with malonic esters and CO2 to form two C(sp3)–C bonds has been developed. The reaction proceeds at room temperature with 0.1 mol% of the organic photocatalyst (4DPAIPN) and cesium carbonate as a base at a CO2 pressure of 4 atm. This results in the production of 3‐arylpropane‐1,1,3‐tricarboxylic acid esters in yields ranging from 48% to 99%.

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Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO₂

Kharlamova,

Averin,

Bondarenko

et al. 2024

Adv Synth Catal

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DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes

Ding,

Yang,

Luo

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryHerein, we report a rare example of three‐component net‐oxidative sulfonylation of a SO2 surrogate with an oxidatively activated radical precursor under mild and metal‐ and external‐oxidant‐free conditions. The mildness and sustainability of the reaction are enabled by photoelectrocatalysis, and 3‐aza‐1,5‐dienes, organotrifluoroborates and 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in an atom‐economical manner with a broad substrate scope and good functional‐group tolerance. The protocol is amenable to the late‐stage diversification of complex molecular architectures as well as the gram‐scale synthesis. Sunlight could be used as the light source, and the reaction could be conducted in an all‐solar mode using a commercially available photovoltaic panel to generate electricity in situ. Mechanistic studies reveal that the in situ generated 1,4‐diazabicyclo[2.2.2]octane (DABCO), which was generally innocent in previous reactions, functions as an electron shuttle between the photocatalytic cycle and the reactants.

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Recent advances of 3DPAFIPN in photoredox catalysis

Yadav,

Singh,

Murti

et al. 2024

Tetrahedron

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Visible-light-driven alkene dicarboxylation with formate and CO₂ under mild conditions

Abstract: The low-cost formate salt was used as the reductant and part of the carboxyl source in a visible-light-driven dicarboxylation of diverse alkenes, including simple styrenes. The highly competing hydrocarboxylation side...

Cited by 11 publications

References 95 publications

Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO₂

Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO₂

DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes

Recent advances of 3DPAFIPN in photoredox catalysis

Contact Info

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Resources

About

Visible-light-driven alkene dicarboxylation with formate and CO2 under mild conditions

Abstract: The low-cost formate salt was used as the reductant and part of the carboxyl source in a visible-light-driven dicarboxylation of diverse alkenes, including simple styrenes. The highly competing hydrocarboxylation side...

Cited by 11 publications

References 95 publications

Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO2

Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO2

DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes

Recent advances of 3DPAFIPN in photoredox catalysis

Contact Info

Product

Resources

About

Visible-light-driven alkene dicarboxylation with formate and CO₂ under mild conditions

Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO₂

Visible Light Photoredox‐Catalyzed Three‐Component Reaction of Styrenes with Malonic Esters and CO₂