Electrochemical Cross-Coupling Reactions between Arylboronic Esters and Aryllithiums Using NaBr as a Halogen Mediator

Koichi Mitsudo; Keisuke Shigemori; Taro Shibata; Hiroki Mandai; Eisuke Sato; Seiji Suga

doi:10.1055/a-2034-9821

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2999-3004
DOI: 10.1055/a-2034-9821

paper

Special Issue Electrochemical Organic Synthesis

Electrochemical Cross-Coupling Reactions between Arylboronic Esters and Aryllithiums Using NaBr as a Halogen Mediator

Koichi Mitsudo ∗

^aDivision of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan

,

Keisuke Shigemori

^aDivision of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan

,

Taro Shibata

^aDivision of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan

,

Hiroki Mandai

^bDepartment of Pharmacy, Faculty of Pharmacy, Gifu University of Medical Science, 4-3-3 Nijigaoka, Kani, Gifu 509-0293, Japan

,

Eisuke Sato

^aDivision of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan

,

Seiji Suga∗

^aDivision of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan

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Abstract

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Abstract

An electrochemical cross-coupling reaction between arylboronic esters and aryllithiums was developed. The presence of Br^– in the electrolyte was found to be essential for the reaction. NaBr was chosen as the electrolyte for its inexpensiveness and abundance, and also acted as a halogen mediator. The reaction proceeded under mild conditions to afford biaryls.

Key words

electro-oxidation - anodic oxidation - cross-coupling - transition-metal-free - biaryl

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References

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Supplementary Material

Supporting Information