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Solid-supported acids as mild and versatile reagents for the deprotection of aromatic ethers
Authors:Ploypradith Poonsakdi  Cheryklin Pannarin  Niyomtham Nattisa  Bertoni Daniel R  Ruchirawat Somsak
Institution:Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vipavadee-Rangsit Highway, Bangkok, Thailand 10210. poonsakdi@cri.or.th
Abstract:p-Toluene sulfonic acid (p-TsOH) immobilized either on polystyrene (PS) or silica (Si) was found to be effective in cleaving aromatic ethers containing isopropyl, tert-butyl, allyl, and benzyl groups, as well as mono-, di-, and trimethoxylated benzyl groups, in moderate to excellent yields (54-95%). These protecting groups could be selectively deprotected when they were simultaneously present on the same or different aromatic rings in a substrate.
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