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Rapid and Mild Cleavage of Aryl‐Alkyl Ethers to...
Journal article

Rapid and Mild Cleavage of Aryl‐Alkyl Ethers to Liberate Phenols

Abstract

Abstract We report that the Piers‐Rubinsztajn reaction enables rapid deprotection of aryl alkyl ethers under ambient conditions. This chemistry leverages tris(pentafluorophenyl)borane and silyl hydrides to convert aryl methyl ethers to siloxanes, which can then be cleaved using 1 % HCl in EtOH. We examined 26 derivatives and routinely obtained yields >85 %, even in the presence of sterically demanding groups and complex substrate structures. …

Authors

Torrens AA; Ly AL; Fong D; Adronov A

Journal

European Journal of Organic Chemistry, Vol. 2022, No. 27,

Publisher

Wiley

Publication Date

July 21, 2022

DOI

10.1002/ejoc.202200570

ISSN

1434-193X