Flash Electrochemical Approach to Carbocations

Masahiro Takumi; Hodaka Sakaue; Aiichiro Nagaki

doi:10.1002/anie.202116177

Flash Electrochemical Approach to Carbocations

Angew Chem Int Ed Engl. 2022 Mar 1;61(10):e202116177. doi: 10.1002/anie.202116177. Epub 2022 Jan 13.

Authors

Masahiro Takumi¹, Hodaka Sakaue¹, Aiichiro Nagaki¹

Affiliation

¹ Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura Nishikyo-ku, Kyoto, 615-8510, Japan.

PMID: 34931424
DOI: 10.1002/anie.202116177

Abstract

A novel flow electrochemical reactor that accomplishes electrolysis within a few seconds in a single passage was developed. By using the flow reactor system, the flash electrochemical generation of short-lived carbocations, including oxocarbenium ions, N-acyliminium ions, glycosyl cations, and Ferrier cations was achieved within a few seconds, enabling the subsequent reaction with nucleophiles before their decomposition. Moreover, continuous operation based on the present system enabled the rapid synthesis of pharmaceutical precursors on demand.

Keywords: Carbocations; Electrochemistry; Flow Chemistry; Glycosylation; Microreactor.

Publication types

Research Support, Non-U.S. Gov't