Al(III) -catalysed formation of poly(limonene)carbonate: DFT analysis of the origin of stereoregularity

Chemistry : a European Journal
Leticia Peña CarrodeguasArjan W Kleij

Abstract

Amino-triphenolate derived Al(III) complexes combined with suitable nucleophiles have been investigated as binary catalysts for the coupling of limonene oxide and carbon dioxide to afford alternating polycarbonates. These catalysts are able to produce stereoregular, perfectly alternating trans-polymers from cis-limonene oxide, whereas the pure trans isomer and cis/trans mixture give rise to lower degrees of stereoregularity. The best Al(III) catalyst shows the potential to mediate the conversion of both stereoisomers of limonene oxide with high conversion levels of up to 71 % under neat conditions, indicating the high degree of robustness and atom-efficiency of this catalytic process. Computational studies have revealed unique features of the binary catalyst system, among which is the preferred nucleophilic attack on the quaternary carbon centre in the limonene oxide substrate.

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Citations

Feb 20, 2016·Angewandte Chemie·Jeroen RintjemaArjan W Kleij
Sep 20, 2015·Angewandte Chemie·Wusheng GuoArjan W Kleij
Jun 16, 2016·Nature Communications·O HauensteinA Greiner
Dec 23, 2015·Chemistry : a European Journal·Wusheng GuoArjan W Kleij
Aug 8, 2018·ChemSusChem·Arjan W Kleij
Apr 16, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Kenson AmbroseChristopher M Kozak
Jul 6, 2019·Chemical Society Reviews·Bruno GrignardChristophe Detrembleur
Dec 10, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Arron C DeacyCharlotte K Williams
Mar 16, 2017·Natural Product Reports·Samantha L KristufekKaren L Wooley
May 6, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Hart PlommerFrancesca M Kerton
Sep 5, 2020·Angewandte Chemie·Thomas T D ChenCharlotte K Williams
Dec 1, 2018·Inorganic Chemistry·Arron C DeacyCharlotte K Williams

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