Journal
MOLECULES
Volume 27, Issue 16, Pages -Publisher
MDPI
DOI: 10.3390/molecules27165342
Keywords
catalysis; green chemistry; natural product; photocatalysis; photosensitizer; (E; Z)-isomerization; diastereoselective dihydroxylation; DFT calculations; calculation of triplet energy
Funding
- Deutsche Forschungsgemeinschaft (DFG)
- GRK [2515]
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In this study, natural product (E)-anethole was successfully isomerized to (Z)-anethole using a self-designed cheap photoreactor. The selection of an appropriate photosensitizer, Ir(p-tBu-ppy)(3), was supported by theoretical predictions of the triplet energies of (E)- and (Z)-anethole. The reaction achieved high conversion with a catalyst loading of only 0.1 mol% and mild irradiation conditions. Diastereomerically pure diols with different configurations were obtained through dihydroxylation.
Natural product (E)-anethole was isomerized to (Z)-anethole in a photocatalytic reaction. For this purpose, a self-designed cheap photoreactor was constructed. Among 11 photosensitizers (organo and metal complex compounds), Ir(p-tBu-ppy)(3) led to the highest conversion. Triplet energies of (E)- and (Z)-anethole were predicted theoretically by DFT calculations to support the selection of appropriate photosensitizers. A catalyst loading of 0.1 mol% gave up to 90% conversion in gram scale. Further additives were not required and mild irradiation with light of 400 nm overnight was sufficient. As a proof of concept, (E)- and (Z)-anethole were dihydroxylated diastereoselectively to obtain diastereomerically pure like- and unlike-configured diols, respectively.
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