Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers

Org Lett. 2024 Dec 27;26(51):11111-11116. doi: 10.1021/acs.orglett.4c03928. Epub 2024 Dec 16.

Abstract

Catalysts for Claisen rearrangement have been intensively studied to overcome the need for high temperature. However, previous studies have encountered challenges, such as the need for heating, a long reaction time, and/or the need for equivalent amounts of catalyst. In this study, we introduce an effective electrogenerated boron-based Lewis acid catalyst for the aromatic Claisen rearrangement, which proceeds in a few minutes at ambient temperature. Generation of the electrogenerated Lewis acid catalyst is discussed based on NMR analysis and DFT calculations.