Solid-supported acids as mild and versatile reagents for the deprotection of aromatic ethers |
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Authors: | Ploypradith Poonsakdi Cheryklin Pannarin Niyomtham Nattisa Bertoni Daniel R Ruchirawat Somsak |
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Affiliation: | Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vipavadee-Rangsit Highway, Bangkok, Thailand 10210. poonsakdi@cri.or.th |
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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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