Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group

Chemoselective deprotection of triethylsilyl ethers.

An efficient and selective method was developed for the deprotection of triethylsilyl (TES) ethers using formic acid in methanol (5-10%) or in methylene chloride 2-5%) with excellent yields. TES ethers are selectively deprotected to the corresponding alcohols in high yields using formic acid in methanol under mild reaction conditions. Other hydroxyl protecting groups like t-butyldimethylsilyl (...

Strategies for Protecting Group Free Glycosidation

Oxidative photoredox catalysis: mild and selective deprotection of PMB ethers mediated by visible light.

Herein we report an advancement in the application of visible light photoredox catalysts in the oxidation of electron-rich arenes resulting in the selective deprotection of para-methoxybenzyl (PMB) ethers. This method is highlighted by excellent functional group tolerance, protecting group orthogonality, mild reaction conditions and avoidance of stoichiometric redox byproducts.

tert-Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

The tert-butoxy derivative is one of the most underused alcohol protecting groups. After having developed an easy and useful protocol for its introduction, we offer here a simple procedure for its removal by treatment with anhydrous CeCl3 and NaI in CH3CN. The procedure led to the successful cleavage of aliphatic and aromatic tert-butyl ethers and was compatible with various other functionaliti...

Ammonium Decatungstocerate(IV): An Efficient Catalyst for the Protection and Deprotection of Tetrahydropyranyl Ethers

In multi-step organic syntheses, the protection and deprotection of tetrahydropyranyl (THP) ethers is one of the most frequently used methods. Over the years, different methods have been used from various catalytic systems for the protection of hydroxyl groups as THP ethers and their deprotection. Herein we have reported that various alcohols and phenols have been efficiently converted to the c...