Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis

Yunxiao Zhang, Yizhi Zhang, Chen Ye, Xiaotian Qi (), Li-Zhu Wu () and Xiao Shen ()
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Yunxiao Zhang: Wuhan University
Yizhi Zhang: Wuhan University
Chen Ye: Chinese Academy of Sciences
Xiaotian Qi: Wuhan University
Li-Zhu Wu: Chinese Academy of Sciences
Xiao Shen: Wuhan University

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: Abstract Developing photo-induced cascade cyclization of alkene-tethered acylsilanes is challenging, because acylsilanes are unstable under light irradiation. Herein, we report that the energy transfer from excited acylsilanes to a photocatalyst that possesses lower triplet energy can inhibit the undesired decomposition of acylsilanes. With neutral Eosin Y as the photocatalyst, an efficient synthesis of cyclopentanol derivatives is achieved with alkene-tethered acylsilanes and allylic sulfones. The reaction shows broad substrate scope and the synthetic potential of this transformation is highlighted by the construction of cyclopentanol derivatives which contain fused-ring or bridged-ring.

Date: 2022
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DOI: 10.1038/s41467-022-33730-x

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