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Abstract
This review presents the recent advances involving several applications of five-membered cyclic carbonates and derivatives. With more than 150 references, it covers the period from 2012 to 2020, with special emphasis on the use of five-membered cyclic carbonates as building blocks for organic synthesis and material elaboration. We demonstrate the application of cyclic carbonates in several important chemical transformations, such as decarboxylation, hydrogenation, and transesterification reactions, among others. The presence of cyclic carbonates in molecules with high biological potential is also displayed, together with the importance of these compounds in the preparation of materials such as urethanes, polyurethanes, and flame retardants.
Highlights
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Among the above-mentioned substrates, glycerol derivatives are important starting materials, which have been widely exploited for different applications, such as their potent antiwear action when added to fuels [8]
Gly2coefr5o6l carbonate (GC) 1a was used as a monomer in the synthesis of hyperbranched aliphatic polyethers [9] and polyurethanes [10]
Summary
Catalytic hydrogenation of organic carbonates is of synthetic interest a5sofa5n6 environmentally benign approach to fundamental synthetic building blocks, such as alcohols and diols [34,35]. The expected unsaturated 1,4-diols 9 were obtained with 50–98% yields with >99:1 Z-stereoselectivity (Scheme 22) While different groups such as aryl, naphthyl, and heteroaryl were efficiently incorporated into diols 9, it is important to highlight that some specific substitutions, e.g., o-haloaryl or 3-pyridyl, required forced conditions with higher temperatures and larger amounts of Pd-catalyst (5 mol%) and phosphine ligand (10 mol%) in order to reach preparative yields. Sci. 2021, 11, x FOR PEER REVIEW unsaturated 1,4-diols 9 were obtained with 50–98% yields with >99:1 Z-stereoselectivity (Scheme 22) Preparation of poly(ethyleneimine)s (PEI) and amphiphilic monodisperse compounds
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