Synthesis of α-allenic aldehydes/ketones from homopropargylic alcohols using a visible-light irradiation system

A visible-light irradiation tandem oxidative aryl migration/carbonyl formation reaction, mediated by K 2 S 2 O 8 and visible-light photoredox catalysis, has been discovered. The presented transformation provides a straightforward access to important α-allenic aldehyde/ketone derivatives from readily...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-06, Vol.21 (25), p.524-5244
Main Authors: Jiang, Dong-Fang, Zeng, Xing-Xing, Li, De-Feng, Wen, Si-Miaomiao, Hu, Ming-Hua
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Aromatic compounds
Carbonyl compounds
Carbonyls
Catalysis
Irradiation
Ketones
Light irradiation
Photoredox catalysis
Potassium persulfate
Substrates
Synthesis
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Summary:A visible-light irradiation tandem oxidative aryl migration/carbonyl formation reaction, mediated by K 2 S 2 O 8 and visible-light photoredox catalysis, has been discovered. The presented transformation provides a straightforward access to important α-allenic aldehyde/ketone derivatives from readily available homopropargylic alcohol derivatives in a regioselective manner of 1,4-aryl shift concomitant with carbonyl formation. The operational simplicity and broad substrate scope demonstrate the great potential of this method for the synthesis of highly functional α-allenic aldehyde/ketone derivatives. A visible-light irradiation tandem oxidative aryl migration/carbonyl formation reaction, mediated by K 2 S 2 O 8 and visible-light photoredox catalysis, has been discovered.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00664f