Abstract
The development of eco-compatible and economically competitive methods enabling carbohydrate transformation into high-added value sugar-based derivatives is highly desirable to promote their valorization as petroleum-based chemical alternatives. We propose in this study a one-pot sequential procedure for the synthesis of sugar amides, used in various areas from detergency to medicine, starting from nonprotected abundant carbohydrates. The use of a small amount of a recyclable gold catalyst (0.36 mol % Au, Au/CeO2) is crucial for promoting the oxidative amidation reaction. In the presence of benzylamine, D-xylose (the main monomer of hemicellulose used as a model) was converted into corresponding benzyl xylonamide in 3 h at room temperature under an O2 atmosphere. The optimized conditionswere then successfully applied to a series of abundant carbohydrates (glucose, galactose, and maltose) and a wide range of amines, thus demonstrating the procedure’s versatility. It is established as not sugar-dependent while being compatible with various functional groups such as alkene, alkyne, thiol, and hydroxyl. Finally, the greenness of the procedure was assessed by comparing the synthesis of N-decyl-D-xylonamide using four green metrics, underlining lower waste generation, higher atom economy, and more acceptable reaction conditions in terms of environmental impact.