Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process

Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developed via the reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-10, Vol.19 (39), p.852-856
Main Authors: Lei, Wan, Liu, Yongjun, Fang, Yewen, Li, Yan, Du, Chan, Fang, Jianghua
Format: Article
Language:English
Subjects:
Catalysis
Crossovers
Deuteration
Ketones
Photoredox catalysis
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Summary:Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developed via the reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated. New access to allenes: With photocatalytic reductive radical-polar crossover as the strategy, a new protocol for the preparation of trisubstituted allenes has been nicely developed via the reactions of 1,3-enynes with various alkyl radicals.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01654g