Catalytic amidation of natural and synthetic polyol esters with sulfonamides.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 31462632.
- Also identified by DOI 10.1038/s41467-019-11864-9 and PMC identifier 6713792.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
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(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 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.