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. 2022 Dec 5;61(49):e202212131.
doi: 10.1002/anie.202212131. Epub 2022 Nov 4.

Electrochemical Palladium-Catalyzed Oxidative Carbonylation-Cyclization of Enallenols

Jianwei Zhang  1 , Biswanath Das  1 , Oscar Verho  2 , Jan-E Bäckvall  1
Affiliations

Electrochemical Palladium-Catalyzed Oxidative Carbonylation-Cyclization of Enallenols

Jianwei Zhang et al. Angew Chem Int Ed Engl. .

Abstract

Herein, we report an electrochemical oxidative palladium-catalyzed carbonylation-carbocyclization of enallenols to afford γ-lactones and spirolactones, which proceeds with excellent chemoselectivity. Interestingly, electrocatalysis was found to have an accelerating effect on the rate of the tandem process, leading to a more efficient reaction than that under chemical redox conditions.

Keywords: Anodic Oxidation; Electrocatalysis; Enallenol; Palladium; Undivided Cell.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Examples of Pd‐catalyzed electrochemical C−H functionalization.
Scheme 2
Scheme 2
Electrooxidative Pd‐catalyzed C−H functionalization.
Scheme 3
Scheme 3
Scope for selective formation of γ‐lactones 3.
Scheme 4
Scheme 4
Scope for selective formation of spirolactones 5.
Scheme 5
Scheme 5
Gram‐scale electrolysis.
Scheme 6
Scheme 6
Proposed catalytic cycle.
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