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Photocatalytic Synthesis of Dihydrobenzofurans by Oxidative [3+2] Cycloaddition of Phenols
Author(s) -
Blum Travis R.,
Zhu Ye,
Nordeen Sarah A.,
Yoon Tehshik P.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406393
Subject(s) - cycloaddition , chemistry , photocatalysis , photoredox catalysis , ammonium persulfate , oxidative phosphorylation , phenols , persulfate , catalysis , organic chemistry , visible spectrum , photochemistry , combinatorial chemistry , materials science , biochemistry , polymer , polymerization , optoelectronics
We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible‐light‐activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled, benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis suggests that this strategy may be applicable to a variety of useful oxidative transformations.