Catalytic, regioselective sulfonylation of carbohydrates with dibutyltin oxide under solvent‐free conditions

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Abstract

A simple approach was developed for the solvent‐free regioselective functionalization of carbohydrate polyols with 4‐toluesulfonyl (tosyl) group, allowing the easy and quick activation of a saccharide site with a tosylate leaving group. The method is based on the use of catalytic dibutyltin oxide and tetrabuylammonium bromide (TBAB), and a moderate excess of N,N‐diisopropylethyl amine (DIPEA) and tosyl chloride (TsCl), leading to the selective functionalization at 75 °C of a secondary equatorial hydroxy function flanked by an axial one in a pyranoside. The procedure is endowed with several advantages, such as the use of cheap reagents, experimental simplicity, and the need for reduced reaction times in comparison with other known approaches.

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Traboni, S., Bedini, E., Landolfi, A., Vessella, G., & Iadonisi, A. (2021). Catalytic, regioselective sulfonylation of carbohydrates with dibutyltin oxide under solvent‐free conditions. Catalysts, 11(2), 1–9. https://doi.org/10.3390/catal11020202

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