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Updated: May 23, 2025

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Ammoxidation of Unprotected Glycosides: A One-Pot Conversion of Alcohols to Nitriles
Jacob-Jan Haaksma1, J Prathap Kaniraj1, Wiktoria M Opielak1
1Stratingh Institute for Chemistry, University of Groningen, 9747 AG, Groningen, The Netherlands.
Abstract:
Functionalized carbohydrates are important in various fields, but protection-free selective functionalization often remains challenging. We demonstrate that the primary hydroxy group in minimally protected carbohydrates can be directly converted into a nitrile group with TEMPO, PIDA, and ammonium acetate. Both nitrile hexopyranoses and nitrile pentofuranoses are obtained and subsequent derivatizations of the nitrile group to other versatile functional groups are demonstrated. Combined evidence from literature and in-situ reaction progress monitoring with Raman spectroscopy led to the proposal that iminoiodinanes derived from PIDA play an important role in the mechanism of ammoxidation.
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