Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 9, Pages 2459-2463Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711599
Keywords
alkenes; chalcogen Lewis acids; hydrogen phosphates; oxidation; photoredox catalysis
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Funding
- German Research Foundation (Emmy Noether Fellowship) [4907/1-1]
- Fonds der Chemischen Industrie
- Lower Saxony Ministry for Science and Culture (Georg-Christoph-Lichtenberg Fellowship)
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A catalytic regime for the direct phosphatation of simple, non-polarized alkenes has been devised that is based on using ordinary, non-activated phosphoric acid diesters as the phosphate source and O-2 as the terminal oxidant. The title method enables the direct and highly economic construction of a diverse range of allylic phosphate esters. From a conceptual viewpoint, the aerobic phosphatation is entirely complementary to traditional methods for phosphate ester formation, which predominantly rely on the use of prefunctionalized or preactivated reactants, such as alcohols and phosphoryl halides. The title transformation is enabled by the interplay of a photoredox and a selenium pi-acid catalyst and involves a sequence of single-electron-transfer processes.
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