Photocatalyzed Dehydration of 1-Aryl-1,2-Ethanediols to Methyl Ketones Driven by Eosin Y Fragmentation Products.

Autor: Taskinen EK; Department of Chemistry and Pharmacy, University of Regensburg, Universitätstr. 31, 93053, Regensburg, Germany., Kolb D; Department of Chemistry and Pharmacy, University of Regensburg, Universitätstr. 31, 93053, Regensburg, Germany., Morgenstern M; Department of Chemistry and Pharmacy, University of Regensburg, Universitätstr. 31, 93053, Regensburg, Germany., König B; Department of Chemistry and Pharmacy, University of Regensburg, Universitätstr. 31, 93053, Regensburg, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Dec 08, pp. e202404200. Date of Electronic Publication: 2024 Dec 08.
DOI: 10.1002/chem.202404200
Abstrakt: Herein, we report a mild photocatalytic redox-neutral dehydration of aryl-1,2-ethanediols forming the respective methyl ketones. In the proposed mechanistic cycle an initial hydrogen atom abstraction (HAT) is followed by a 1,2-spin center shift (SCS) as key steps. Interestingly, Eosin Y was found to act as a pre-catalyst dissociating into a catalytically active mixture under irradiation. To the best of our knowledge, this exemplifies the first synthetic utilization of Eosin Y degradation products. As a result, our reaction can be realized with a single organic photocatalyst and releases water as a sole by-product.
(© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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