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 K2S2O8 and visible-light photoredox catalysis, has been discovered. The presented transformation provides a straightforward access to important alpha-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 alpha-allenic aldehyde/ketone derivatives.

Automated summary

A tandem oxidative aryl migration/carbonyl formation reaction mediated by K2S2O8 and visible-light photoredox catalysis has been discovered, which enables the synthesis of important alpha-allenic aldehyde/ketone derivatives in a regioselective manner through 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 alpha-allenic aldehyde/ketone derivatives.