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

Xintao Gu; Yin Wei; Min Shi

doi:10.1039/D1QO01373D

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

Xintao Gu,^a Yin Wei*^b and Min Shi

*^ab

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* Corresponding authors

^a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People's Republic of China

^b State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: mshi@sioc.ac.cn

Abstract

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.

This article is part of the themed collection: 2021 Organic Chemistry Frontiers HOT articles

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DOI: https://doi.org/10.1039/D1QO01373D
Article type: Research Article
Submitted: 14 Sep 2021
Accepted: 02 Nov 2021
First published: 04 Nov 2021

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Org. Chem. Front., 2021,8, 6823-6829

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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

X. Gu, Y. Wei and M. Shi, Org. Chem. Front., 2021, 8, 6823 DOI: 10.1039/D1QO01373D

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Organic Chemistry Frontiers

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

Abstract

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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

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