One-Pot Synthesis of Aryl Selenonic Acids and some Unexpected Byproducts
Date
2021-07-16
Journal Title
Journal ISSN
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Publisher
ASC Publications
Abstract
The synthesis of aryl selenonic acids was achieved from diverse aryl bromides via a one-pot method involving metalation, selenation and oxidation with hydrogen peroxide, followed by ion exchange to afford the pure products in 77-90% yield. An o-hydroxymethyl derivative was found to dehydrate readily, affording the first example of a cyclic selenonic ester, while two minor byproducts were isolated and shown by x-ray crystallography to be mixed salts of aryl selenonic acids with either the corresponding aryl seleninic or selenious acid.
Description
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher.
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Citation
Sands, K. N., Gelfand, B. S., & Back, T. G. (2021). One-Pot Synthesis of Aryl Selenonic Acids and Some Unexpected Byproducts. The Journal of Organic Chemistry.