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      Chemo‐ and Regioselective Additions of Nucleophiles to Cyclic Carbonates for the Preparation of Self‐Blowing Non‐Isocyanate Polyurethane Foams

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          Abstract

          Polyurethane (PU) foams are indisputably daily essential materials found in many applications, notably for comfort (for example, matrasses) or energy saving (for example, thermal insulation). Today, greener routes for their production are intensively searched for to avoid the use of toxic isocyanates. An easily scalable process for the simple construction of self‐blown isocyanate‐free PU foams by exploiting the organocatalyzed chemo‐ and regioselective additions of amines and thiols to easily accessible cyclic carbonates is described. These reactions are first validated on model compounds and rationalized by DFT calculations. Various foams are then prepared and characterized in terms of morphology and mechanical properties, and the scope of the process is illustrated by modulating the composition of the reactive formulation. With impressive diversity and accessibility of the main components of the formulations, this new robust and solvent‐free process could open avenues for construction of more sustainable PU foams, and offers the first realistic alternative to the traditional isocyanate route.

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          Most cited references40

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          Recent Advances in the Catalytic Preparation of Cyclic Organic Carbonates

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            On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane.

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              Sustainable conversion of carbon dioxide: the advent of organocatalysis

              The conversion of carbon dioxide (CO 2 ), an abundant renewable carbon reagent, into chemicals of academic and industrial interest is of imminent importance to create a higher degree of sustainability in chemical processing and production. The conversion of carbon dioxide (CO 2 ), an abundant renewable carbon reagent, into chemicals of academic and industrial interest is of imminent importance to create a higher degree of sustainability in chemical processing and production. Recent progress in this field is characterised by a plethora of organic molecules able to mediate the conversion of suitable substrates in the presence of CO 2 into a variety of value-added commodities with advantageous features combining cost-effectiveness, metal-free transformations and general substrate activation profiles. In this review, the latest developments in the field of CO 2 catalysis are discussed with a focus on organo-mediated conversions and their increasing importance in serving as practicable alternatives for metal-based processes. Also a critical assessment of the state-of-the-art methods is presented with attention to those features that need further development to increase the usefulness of organocatalysis in the production of organic molecules of potential commercial interest.
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                Author and article information

                Contributors
                (View ORCID Profile)
                Journal
                Angewandte Chemie International Edition
                Angew Chem Int Ed
                Wiley
                1433-7851
                1521-3773
                September 21 2020
                July 29 2020
                September 21 2020
                : 59
                : 39
                : 17033-17041
                Affiliations
                [1 ] Center for Education and Research on Macromolecules (CERM) CESAM Research Unit University of Liège Department of Chemistry Sart-Tilman, B6A 4000 Liège Belgium
                [2 ] Institut des Sciences Moléculaires (ISM) UMR5255 CNRS Université de Bordeaux 351 Cours de la libération 33405 Talence Cedex France
                Article
                10.1002/anie.202006267
                15785df5-fa3c-4165-ad71-6249e36a9b97
                © 2020

                http://onlinelibrary.wiley.com/termsAndConditions#vor

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