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A Novel Catalytic Route to Polymerizable Bicyclic Cyclic Carbonate Monomers from Carbon Dioxide.
Qiao, Chang; Shi, Wangyu; Brandolese, Arianna; Benet-Buchholz, Jordi; Escudero-Adán, Eduardo C; Kleij, Arjan W.
Afiliação
  • Qiao C; Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
  • Shi W; Universitat Rovira i Virgili, C/Marcel ⋅ lí Domingo s/n, 43007, Tarragona, Spain.
  • Brandolese A; Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
  • Benet-Buchholz J; Universitat Rovira i Virgili, C/Marcel ⋅ lí Domingo s/n, 43007, Tarragona, Spain.
  • Escudero-Adán EC; Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
  • Kleij AW; Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
Angew Chem Int Ed Engl ; 61(27): e202205053, 2022 Jul 04.
Article em En | MEDLINE | ID: mdl-35441777
A new catalytic route has been developed for the coupling of epoxides and CO2 affording polymerizable six-membered bicyclic carbonates. Cyclic epoxides equipped with a ß-positioned OH group can be transformed into structurally diverse bicyclic cyclic carbonates in good yields and with high selectivity. Key to the chemo-selectivity is the difference between the reactivity of syn- and anti-configured epoxy alcohols, with the latter leading to six-membered ring carbonate formation in the presence of a binary AlIII aminotriphenolate complex/DIPEA catalyst. X-ray analyses show that the conversion of the syn-configured substrate evolves via a standard double inversion pathway providing a five-membered carbonate product, whereas the anti-isomer allows for activation of the oxirane unit of the substrate opposite to the pendent alcohol. The potential use of these bicyclic products is shown in ring-opening polymerization offering access to rigid polycarbonates with improved thermal resistance.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2022 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2022 Tipo de documento: Article