Catalytic amidation of natural and synthetic polyol esters with sulfonamides

Hua Liu, Yi-Ling Zhu and Zhi Li ()
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Hua Liu: ShanghaiTech University
Yi-Ling Zhu: ShanghaiTech University
Zhi Li: ShanghaiTech University

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Triacylglycerides are naturally abundant and renewable feedstock for biofuels and chemicals. In this report, these seemingly stable compounds are shown to be reactive toward a variety of sulfonamides under Lewis acid catalysis. In these reactions, alkyl C(sp3)–O bonds are cleaved and C–N bonds constructed, providing functionalized value-added products directly from renewables. Mechanistic and scope study demonstrate that the origin of the reactivity could be the synergy of Lewis acid catalysis and neighboring group participation by the 2- or 3-acyloxy or acylamido group with respect to the reactive site. Since poly(ethylene terephthalate) (PET), a widely available consumer polyester, also contains 1,2-diol diester group as the repeating unit in the main chain, this chemistry can also be applied to efficient depolymerization of PET.

Date: 2019
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DOI: 10.1038/s41467-019-11864-9

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