Issue 24, 2021

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
14 सितम्बर 2021
Accepted
02 नवम्बर 2021
First published
04 नवम्बर 2021

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

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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