One-Pot Cleavage of Aryl Alkyl Ethers by Aluminum and Iodine in Acetonitrile

摘要

Cleavage of aryl alkyl ethers was conducted in a one-pot onestage manner by mixing the ethers,aluminum and iodine in acetonitrile without the in situ preparation of aluminum triiodide in advance.For ethers bearing acid-labile functional groups such as allyl,alkenyl and carbonyl,an acid scavenger(calcium oxide,1,3-diisopropylcarbodiimide or dimethyl sulfoxide)was used to prevent side-reactions.This one-pot protocol is efficient and convenient for the removal of methyl,ethyl,isopropyl and tert-butyl groups from typical aryl alkyl ethers,catechol monomethyl and dimethyl ethers,and is compatible with a variety of functional groups including alkenyl,alkyl,allyl,amido,cyano,formyl,halogen,keto and nitro group.Methyl 2-anisate and eugenol acetate were exhaustively deprotected by the method that afforded salicylic acid and hydroxychavicol,respectively.