Journal
GREEN CHEMISTRY
Volume 23, Issue 1, Pages 296-301Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0gc03613g
Keywords
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Funding
- National Key Research and Development Program of China [2020YFA0608300]
- NSFC [21772163, 21778042]
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Metal-free, visible-light-induced denitrogenative phosphorylation of 1,2,3-benzotriazinones was achieved using eosin Y as a photoredox catalyst. The method allows for efficient synthesis of aryl-phosphonates, aryl-phosphinates, and aryl-phosphine oxides under sunlight or a blue LED as a light source, demonstrating clean reaction profile, energy efficiency, and broad substrate scope.
Metal-free, visible-light-induced denitrogenative phosphorylation of 1,2,3-benzotriazinones was achieved. With the use of eosin Y as a photoredox catalyst, N,N-diisopropylethylamine as a base, CH3CN-H2O as a solvent and sunlight or a blue LED as a light source, a variety of aryl-phosphonates, aryl-phosphinates, and aryl-phosphine oxides were efficiently prepared. In addition, B(2)pin(2) instead of P-nucleophiles as a radical acceptor was also demonstrated. The key advantages of this newly developed method are the clean reaction profile, use of a low-cost organic-dye catalyst, energy efficiency, broad substrate scope, good to excellent yields and large-scale synthetic applicability. The gram-scale synthesised compounds could be isolated in pure form just upon extraction, followed by re-crystallisation; no tedious chromatographic purification was required.
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