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Catalytic amidation of natural and synthetic polyol esters with sulfonamides.

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.

SUBMITTER: Liu H

PROVIDER: S-EPMC6713792 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Catalytic amidation of natural and synthetic polyol esters with sulfonamides.

Liu Hua H Zhu Yi-Ling YL Li Zhi Z

Nature communications 20190828 1

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(sp<sup>3</sup>)-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 ...[more]

PMID: 31462632

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