Electrochemical Palladium-Catalyzed Oxidative Carbonylation-Cyclization of Enallenols

Jianwei Zhang; Biswanath Das; Oscar Verho; Jan-E Bäckvall

doi:10.1002/anie.202212131

Electrochemical Palladium-Catalyzed Oxidative Carbonylation-Cyclization of Enallenols

Angew Chem Int Ed Engl. 2022 Dec 5;61(49):e202212131. doi: 10.1002/anie.202212131. Epub 2022 Nov 4.

Authors

Jianwei Zhang¹, Biswanath Das¹, Oscar Verho², Jan-E Bäckvall¹

Affiliations

¹ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691, Stockholm, Sweden.
² Department of Medicinal Chemistry, Uppsala Biomedical Center, BMC, Uppsala University, 75236, Uppsala, Sweden.

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.

Grants and funding

Department of Medicinal Chemistry/Vetenskapsrådet