Construction of polysubstituted spiro[2.3] or [3.3] cyclic frameworks fused with a tosylated pyrrolidine promoted by visible-light-induced photosensitization,Organic Chemistry Frontiers

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Construction of polysubstituted spiro[2.3] or [3.3] cyclic frameworks fused with a tosylated pyrrolidine promoted by visible-light-induced photosensitization
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-11-04 , DOI: 10.1039/d1qo01373d
Xintao Gu ₁ , Yin Wei ₂ , Min Shi _{1,

2}

Affiliation

Herein, we presented a visible-light-induced intramolecular [2 + 2] cycloaddition of methylenecyclopropanes (MCPs) in the presence of a polypyridyl iridium(III) catalyst for the rapid construction of polysubstituted spiro[2.3] or [3.3] cyclic frameworks fused with a tosylated pyrrolidine in good yields under mild conditions. This newly developed photochemical protocol demonstrates a broad scope on the preparation of spirocyclic skeletons including diversified multi-spiral compounds containing dispiro[2.0.2⁴.2³] and dispiro[2.0.3⁴.2³] frameworks that might be useful in the synthesis of drug like molecules or the other functional materials. The mechanistic paradigm has been investigated on the basis of fluorescence emission quenching analysis, CV measurement and the control experiments, indicating that this visible-light photoinduced [2 + 2] cycloaddition proceeded through a triplet excited state.

中文翻译：

多取代螺[2.3]或[3.3]环状框架的构建与可见光诱导光敏化促进的甲苯磺酰化吡咯烷融合

在此，我们提出了在聚吡啶基铱 ( III ) 催化剂存在下，可见光诱导的亚甲基环丙烷 (MCP) 的分子内 [2 + 2] 环加成反应，用于快速构建多取代的螺[2.3] 或 [3.3] 环状骨架稠合在温和条件下以良好的收率得到甲苯磺酰化的吡咯烷。这种新开发的光化学方案展示了制备螺环骨架的广泛范围，包括含有二螺[2.0.2 ⁴ .2 ³ ] 和二螺[2.0.3 ⁴ .2 ³ ] 的多样化多螺旋化合物] 可能用于合成药物类分子或其他功能材料的框架。在荧光发射猝灭分析、CV 测量和对照实验的基础上研究了机理范例，表明这种可见光光诱导的 [2 + 2] 环加成是通过三重激发态进行的。

更新日期：2021-11-11

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