Enantioselective dearomative ortho-cycloaddition transformation of unactivated arenes by cage-confined visible-light photocatalysis

Jie Yang, Zhongshu Li, Xiantao Wu, Jie Chen, Sisi Huang, Yu-Lin Lu, Zhiwei Jiao () and Cheng-Yong Su ()
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Jie Yang: Sun Yat-Sen University
Zhongshu Li: Sun Yat-Sen University
Xiantao Wu: Sun Yat-Sen University
Jie Chen: Sun Yat-Sen University
Sisi Huang: Sun Yat-Sen University
Yu-Lin Lu: Sun Yat-Sen University
Zhiwei Jiao: Sun Yat-Sen University
Cheng-Yong Su: Sun Yat-Sen University

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract Photoinduced dearomatization of arenes is a powerful strategy in organic synthesis to disrupt the stable aromaticity; however, the asymmetric dearomatization photocatalysis of unactivated arenes remains highly challenging and rare. Herein we demonstrate an enzyme-mimicking cage-confined visible-light asymmetric photocatalysis method for intramolecular dearomative cycloaddition with electron-deficient β-aryl enones. Owing to the multi-functional synergy of chirality, energy transfer, and host-guest interactions in the confined microenvironments, the self-assembled chiral cage-photoreactor could pre-organize the arenes and activate the β-aryl enones to give stereoselectively fused cyclobutanes through visible-light induced [2 + 2] ortho-cycloaddition. Notably, the competing transformation to stable [4 + 2] cycloadducts has been inhibited, producing thermodynamically unfavorable [2 + 2] cycloadducts with excellent regio-, diastereo-, and enantioselectivities.

Date: 2025
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DOI: 10.1038/s41467-025-59176-5

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