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Organocatalytic Polymers from Affordable and Readily Available Building Blocks for the Cycloaddition of CO to Epoxides.
J Org Chem
April 2023
Department of Material Science and Engineering, School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), Payupnai, WangChan, Rayong 21210, Thailand.
The catalytic cycloaddition of CO to epoxides to afford cyclic carbonates as useful monomers, intermediates, solvents, and additives is a continuously growing field of investigation as a way to carry out the atom-economic conversion of CO to value-added products. Metal-free organocatalytic compounds are attractive systems among various catalysts for such transformations because they are inexpensive, nontoxic, and readily available. Herein, we highlight and discuss key advances in the development of polymer-based organocatalytic materials that match these requirements of affordability and availability by considering their synthetic routes, the monomers, and the supports employed.
View Article and Find Full Text PDFTurning Enantiomeric Relationships into Diastereomeric Ones: Self-Resolving α-Ureidophosphonates and Their Organocatalytic Enantioselective Synthesis.
J Am Chem Soc
December 2022
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AGGroningen, The Netherlands.
Controlling chiral recognition and chiral information transfer has major implications in areas ranging from drug design and asymmetric catalysis to supra- and macromolecular chemistry. Especially intriguing are phenomena associated with chiral self-recognition. The design of systems that show self-induced recognition of enantiomers, i.
View Article and Find Full Text PDFVersatile Preparation of Branched Polylactides by Low-Temperature, Organocatalytic Ring-Opening Polymerization in -Methylpyrrolidone and Their Surface Degradation Behavior.
Macromolecules
October 2021
Laboratory of Polymers Biomaterials, Istituto Italiano di Tecnologia, Via Morego 30, 16163 Genoa, Italy.
We describe how the organocatalytic, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-based lactide ring-opening polymerization can be effectively performed in a very polar solvent, -methylpyrrolidone (NMP).
View Article and Find Full Text PDFNeutral Chiral Tetrakis-Iodo-Triazole Halogen-Bond Donor for Chiral Recognition and Enantioselective Catalysis.
Chemistry
February 2021
Organic Chemistry Institute, University of Münster, Corrensstraße 36, 48149, Münster, Germany.
Halogen bonding represents a powerful tool in the field of noncovalent interactions. However, applications in enantioselective recognition and catalysis remain almost nonexistent, due in part to the distinct features of halogen bonds, including long covalent and noncovalent bond distances and high directionality. Herein, this work presents a novel chiral tetrakis-iodo-triazole structure as a neutral halogen bond donor for both chiral anion-recognition and enantioinduction in ion-pair organocatalysis.
View Article and Find Full Text PDFMechanism of Iminium Salt-Catalyzed C(sp)-H Amination: Factors Controlling Hydride Transfer versus H-Atom Abstraction.
ACS Catal
January 2020
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland, 20742-4454, United States.
Carbon-nitrogen bonds are extremely prevalent in pharmaceuticals, natural products, and other biologically relevant molecules such as nucleic acids and proteins. Intermolecular amination of C(sp)-H bonds by catalytic nitrene transfer is a promising method for forging C-N bonds. An organocatalytic approach to nitrene transfer by way of an iminium salt offers a site-selective method for C(sp)-H amination.
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