Copper methanesulfonate-acetic acid as a novel catalytic system for tetrahydropyranylation of alcohols and phenols

A synergistic catalytic effect between copper methanesulfonate and acetic acid in tetrahydropyranylation of alcohols and phenol at room temperature under solvent free condition has been described. Both alcohols （primary, secondary and tertiary） and phenols reacted with 3,4-dihydro-2H-pyran smoothly to afford the corresponding tetrahydropyranyl ethers in good yields.

Regioselective tetrahydropyranylation of alcohols catalyzed by Fe(HSO_4)_3

Alcohols are selectively and efficiently protected as their tetrahydropranyl ethers in the presence of a catalytic amount of Fe（HSO4）3 in good to high yields. All reactions are performed under mild and completely heterogeneous reaction conditions.

Efficient and green tetrahydropyranylation and deprotection of alcohols and phenols by using activated carbon supported sulfuric acid

A simple, green and efficient method for the DHP protection of various alcohols and phenols and the subsequent removal of the corresponding protective group in the presence of a catalytic amount of the activated carbon supported H2SO4 is described.

A Mild and Practical Procedure for Tetrahydropyranylation of Alcohols and Phenols Catalysed by Anhydrous Ferrous Sulfate

An easy preparation of tetrahydropyranyl (THP) ethers of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) in refluxing dichloromethane has been carried out in good to excellent yields under catalysis of anhydrous ferrous sulfate.

Tetrahydropyranylation of Alcohols and Phenols Using Poly- styrene Supported Lewis Acids as Catalysts

Polystyrene supported TiCI4 （Ps-TiCI4） and polystyrene supported FeC13 （Ps-FeC13） were prepared by coordi- nating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyri- dine-adsorbed IR. The loading of Ps-TiC14 and Ps-FeCI3 were 0.35 and 0.3 mmol.g-1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity.

{[K.18-Crown-6]Br_3}_n:A tribromide catalyst for the catalytic protection of amines and alcohols

{[K.18-Crown-6]Br3}n,a unique tribromide-type catalyst,was utilized for the N-boc protection of amines and trimethylsilylation(TMS)and tetrahydropyranylation(THP)of alcohols.The method is general for the preparation of N-boc derivatives of aliphatic(acyclic and cyclic)and aromatic,and primary and secondary amines and also various TMS-ethers and THP-ethers.The simple separation of the catalyst from the product is one of the many advantages of this method.

Selective Monoprotection of Symmetrical Diols in a Flow Reactor

Desymmetrization reactions provide a powerful approach for the construction of complex molecules. Various methods have been developed for the selective monoprotection of symmetrical diols;however, their application to large-scale operations is limited. In this study, the monotetrahydropyranylation of symmetrical diols in a flow reactor has been developed, whereby the length of the flow reactor tube and the amount of acid were optimized. A higher selectivity for the monoprotected derivative was observed when the reaction was performed in a flow reactor compared with that observed in a conventional batch experiment. The efficient flow method developed herein can be applied to large-scale synthesis by numbering up the flow reactor without affecting the selectivity and yield. Since monoprotection can be achieved without using a large excess of diol, our developed flow method is effective when expensive diol must be used.

Efficient oxidative deprotection of trimethylsilyl,tetrahydropyranyl and methoxymethyl ethers under solvent-free conditions

A mild, efficient and fast method for direct oxidation of trimethylsilyl, tetrahydropyranyl and methoxymethyl ethers to their corresponding carbonyl compounds using trinitratocerium（Ⅳ） bromate （TNCB） supported on NaHSO4.H2O under solvent-free conditions is reported.