Issue 25, 2023

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

Abstract

A visible-light irradiation tandem oxidative aryl migration/carbonyl formation reaction, mediated by K2S2O8 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Apr 2023
Accepted
27 May 2023
First published
06 Jun 2023

Org. Biomol. Chem., 2023,21, 5240-5244

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

D. Jiang, X. Zeng, D. Li, S. Wen and M. Hu, Org. Biomol. Chem., 2023, 21, 5240 DOI: 10.1039/D3OB00664F

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