The study presents a novel method for the reductive cleavage of triphenylmethyl (trityl) ethers using triethylsilane (Et3SiH) in the presence of a catalytic amount of triethylsilyl triflate (TESOTf) or trimethylsilyl triflate (TMSOTf). This method allows for the selective protection and subsequent cleavage of primary alcohols in the presence of acid-sensitive functional groups, which is particularly useful in carbohydrate chemistry. The reaction is mild, rapid, and highly chemoselective, with the cleavage process involving an equilibrium between trityl ether, triethylsilyl ether, and trityl cation, leading to the reduction of the trityl cation to triphenylmethane and regeneration of the silyl triflate catalyst. The study demonstrates the effectiveness of this method with a variety of 1,10-decanediol derivatives, sugar derivatives, and trehalose derivatives, showing high yields of the corresponding alcohols after mild acidic treatment. The chemicals used in the study include trityl ethers, triethylsilane, TESOTf, TMSOTf, and various protecting groups such as acetyl, pivaloyl, benzoyl, benzyl, MPM, and TBDPS, which served to protect the primary alcohols during the cleavage process.
