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Relevant academic research and scientific papers

Deprotection of t-butyldimethylsilyl ethers promoted by cerium(IV) triflate

t-Butyldimetylsilyl ethers are mildly cleft by catalytic amounts of cerium(IV) triflate. Dependence from water amount was observed.

Application of SO3H silica gel to deprotection of silyl ethers

A newly developed SO3H silica gel cleaved the O-Si bonds in various aryl and alkyl silyl ethers to give the corresponding phenols and alcohols in good to excellent yield. The crude filtrates contained no silyl residues. The solid phase 29Si NMR analyses of the SO3H silica gel strongly suggested that the silyl residues were captured by silanol groups on the surface of the silica gel. The SO3H silica gel could be recycled at least ten times without any loss of activity. The disappearance of silyl residues in the crude filtrate was observed in even the 10th repetition. Our method provides an easily handled desilylation method that requires no further purification. Our method was also applicable to a selective desilylation reaction of a derivative 5 with different siloxy groups or desilylation of an alkaloid derivative 7.

An environmentally benign synthesis of cis-2,6-disubstituted tetrahydropyrans via indium-mediated tandem allylation/prins cyclization reaction

(Chemical Equation Presented) In the presence of indium metal, 3-iodo-2-[(trimethylsilyl)-methyl]propene (1) reacts with sequentially added aldehydes to provide cis-2,6-disubstituted tetrahydropyrans in good yields. Evidence suggests that InI, formed upon

A mild and selective cleavage of tert-butyldimethylsilyl ethers by indium(III) chloride

Alkyl tert-butyldimethylsilyl ethers are selectively deprotected to the corresponding alcohols in high yields for the first time by indium(III) chloride in refiuxing aqueous acetonitrile. Several functional groups like OBn, Boc, CBz, OBz, O-allyl, OTBDPS, OAc, OMe, ethers, esters and olefins present in the substrate are unaffected.

Chemoselective and practical deprotection of alkyl trialkylsilyl ethers in the presence of aryl trialkylsilyl ethers by a catalytic amount of Sc(OTf)3

Treatment of alkyl trialkylsilyl ethers with 0.5 mol% of Sc(OTf)3 combined with 5 equivalents of water in acetonitrile provides an efficient and practical method for the deprotection of silyl ethers. Alcoholic trialkylsilyl ethers have been cleaved selectively in the presence of phenolic trialkylsilyl ethers.