Solid-supported acids as mild and versatile reagents for the deprotection of aromatic ethers.
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.
Ploypradith
Poonsakdi
P
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vipavadee-Rangsit Highway, Bangkok, Thailand 10210. poonsakdi@cri.or.th
Cheryklin
Pannarin
P
Niyomtham
Nattisa
N
Bertoni
Daniel R
DR
Ruchirawat
Somsak
S
D000143:Acids / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D001557:Benzenesulfonates / Q000737:chemistry; D047188:Chalcones; D004987:Ethers / Q000737:chemistry*; D007202:Indicators and Reagents; D011137:Polystyrenes; D012822:Silicon Dioxide
D000143:Acids; D001547:Benzaldehydes; D001557:Benzenesulfonates; D047188:Chalcones; D004987:Ethers; D007202:Indicators and Reagents; D011137:Polystyrenes; D012822:Silicon Dioxide; C100058:vanillin; C029501:4-toluenesulfonic acid