Citation: Meixin Wang, Yizhi Zhang, Shanshan Liu, Xiao Shen. Synthesis of rigidified cyclohexanes enabled by visible-light-induced trifluoroacetylsilane-mediated [2 + 2] cycloaddition of cyclopropenes[J]. Chinese Chemical Letters, ;2025, 36(8): 110758. doi: 10.1016/j.cclet.2024.110758 shu

Synthesis of rigidified cyclohexanes enabled by visible-light-induced trifluoroacetylsilane-mediated [2 + 2] cycloaddition of cyclopropenes

The Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, Wuhan 430072, China

xiaoshen@whu.edu.cn

Received Date: 2 October 2024
Revised Date: 3 December 2024
Accepted Date: 11 December 2024
Available Online: 12 December 2024

Figures(6)

Imposing conformational constraints on sp³-rich structures is emerging as an important strategy for structural modification and optimization, which can improve the bioactivity of drugs. Herein, we report a visible-light-induced photosensitized [2 + 2] homo-cycloaddition and cross-cycloaddition of cyclopropenes to synthesize tricyclo[3.1.0.0^2,4]hexanes as rigidified 3,3,6,6-tetrasubstituted cyclohexanes. Trifluoroacetylsilanes, previously known as trifluoromethyl siloxycarbene precursors, were used as photocatalysts for the first time. The mechanism study supports that the aggregation of cyclopropenes is important to promote their sensitization by trifluoroacetylsilanes through energy transfer.
- Cyclopropene,
- Tricyclo[3.1.0.0^2,4]hexane,
- Photocycloaddition,
- Mechanism,
- Acylsilane
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