Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 37, Pages 13052-13057Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502450
Keywords
AIBX; carbonyl groups; dehydrogenative functionalization; metal-free synthesis; reaction mechanism
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Funding
- National Natural Science Foundation of China [21172110, 21472094, 21421062]
- Tianjin Natural Science Foundation [09JCYBJC05900]
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We have developed a method for recyclable hypervalent-iodine-mediated direct dehydrogenative ,- bifunctionalization of -ketoesters and -diketones under metal-free conditions, which affords a straightforward way to synthesize benzo-fused 2,3-dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional-group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.
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