Mechanochemical synthesis of nitrogen-functionalized compounds obtained from biomass derivatives

Abstract

In recent years, rapid and wide-ranging developments have established Mechanochemistry as a powerful enabling technology in sustainable synthetic method development. This is mostly due to the ability to perform organic reactions without the need for reaction solvent, often connected with reduced reaction times compared to solution-phase counterparts. There have been a wide array of synthetic organic transformations which have been explored by Mechanochemistry, revealing the synthetic opportunities enabled by the reactor environment of a milling-jar. Benefits of Mechanochemistry include solvent-free reactions, reduced reaction times, improved reaction selectivity and complementary reaction efficiency. Based on recent results obtained in our group, mechanochemical conditions can bring opportunities to enhance several bottlenecks encountered in the dehydration of N-acetylglucosamine at harsh conditions and Diels-Alder reactions with nitrogenated furans, where some Diels-Alder adducts were synthetized using the bio-derived 3-nitrogen-substituted furanic block 3-acetamido-5-etilfuran in solution-phase without any precedence in the literature. Mechanochemistry has a great potential to improve reactivity and selectivity of these reactions, generating further novel bio-based building blocks with higher yields and allowing produtcs than are not accessible at solution-phase, e.g. nitrogen-functionalized aromatic compounds. There are great demand for N-functionalized chemicals in academia and industry for several applications due to their unique chemical properties. (AU)