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

a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Keisuke Shigemori
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Taro Shibata
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Hiroki Mandai
b   Department of Pharmacy, Faculty of Pharmacy, Gifu University of Medical Science, 4-3-3 Nijigaoka, Kani, Gifu 509-0293, Japan
,
Eisuke Sato
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Seiji Suga
a   Division of Applied Chemistry, Graduate School of Natural Science and Technology, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
› Author Affiliations
This work was supported in part by Okayama Foundation for Science and Technology, Wesco Scientific Promotion Foundation, The Sanyo Broadcasting Foundation, Electric Technology Research Foundation of Chugoku, and JSPS KAKENHI grant numbers JP22H02122 (to K.M.), JP22K05115 (to S.S.), and JP21H05214 (Digitalization-driven Transformative Organic Synthesis) (to S.S.).


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.

Supporting Information



Publication History

Received: 15 December 2022

Accepted after revision: 14 February 2023

Accepted Manuscript online:
14 February 2023

Article published online:
15 March 2023

© 2023. Thieme. All rights reserved

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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