Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers.

Org Lett

Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.

Published: December 2024

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.

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http://dx.doi.org/10.1021/acs.orglett.4c03928DOI Listing

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