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

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.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC9573877 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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

Zhang Yunxiao Y Zhang Yizhi Y Ye Chen C Qi Xiaotian X Wu Li-Zhu LZ Shen Xiao X

Nature communications 20221016 1

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 react ...[more]

PMID: 36245017

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