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

Wan Lei; Yongjun Liu; Yewen Fang; Yan Li; Chan Du; Jianghua Fang

doi:10.1039/d1ob01654g

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

Org Biomol Chem. 2021 Oct 14;19(39):8502-8506. doi: 10.1039/d1ob01654g.

Authors

Wan Lei¹, Yongjun Liu¹, Yewen Fang^{2

3}, Yan Li¹, Chan Du², Jianghua Fang²

Affiliations

¹ Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials and Ministry-of-Education Key Laboratory for Synthesis and Application of Organic Functional Molecules, Hubei University, No. 368 YouyiDadao, Wuhan 430062, China. liyanok@hubu.edu.cn.
² School of Materials and Chemical Engineering, Ningbo University of Technology, No. 201 Fenghua Road, Ningbo 315211, China. fang@nbut.edu.cn.
³ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, No.345 Lingling Road, Shanghai 200032, China.

PMID: 34549768
DOI: 10.1039/d1ob01654g

Abstract

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.