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Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols.

ABSTRACT: 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.

SUBMITTER: Blum TR

PROVIDER: S-EPMC4220618 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols.

Blum Travis R TR Zhu Ye Y Nordeen Sarah A SA Yoon Tehshik P TP

Angewandte Chemie (International ed. in English) 20140825 41

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. ...[more]

PMID: 25155300

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