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


We report that the Piers-Rubinsztajn reaction permits quick deprotection of aryl alkyl ethers below ambient circumstances. This chemistry leverages tris(pentafluorophenyl)borane and silyl hydrides to transform aryl methyl ethers to siloxanes, which can then be cleaved working with 1% HCl in EtOH. We examined 26 derivatives and routinely obtained yields >85%, even in the existence of sterically demanding groups and sophisticated substrate constructions. Other alkyl ethers including ethyl, propyl, isopropyl, tert-butyl, and benzyl groups have been also easily eliminated.


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