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

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 yie...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-12, Vol.8 (24), p.6823-6829
Main Authors: Gu, Xintao, Yin, Wei, Shi, Min
Format: Article
Language:English
Subjects:
Catalysts
Chemical synthesis
Cycloaddition
Emission analysis
Emission measurements
Fluorescence
Functional materials
Iridium
Light effects
Organic chemistry
Photochemicals
Photosensitization
Pyrrolidine
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo01373d