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Br-radical-mediated [3+2] annulation: synthesis of 2-bromomethyl-substituted alkenylcyclopentanes by the reaction of alkenylcyclopropanes with allyl bromides under photo irradiation

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Abstract

A radical chain addition of allyl bromides 2 to alkenylcyclopropanes 1 resulted in [3+2] annulation to give 2-bromomethyl-alkenylcyclopentanes 3 in good yields (16 examples). In this reaction, two kinetically fast radical reactions, cyclopropylcarbinyl radical-ring-opening and 5-exo-radical cyclization, preceded the β-fragmentation of a bromine radical to make the formal cycloaddition possible.

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Acknowledgements

This work was supported by a Grant-in-Aid (B) (19H02722) from the Japan Society for the Promotion of Science, and Scientific Research on Innovative Areas 2707 Middle molecular strategy (JP15H05850) from the Ministry of Education, Culture, Sports, Science and Technology. T. Kippo acknowledges a Research Fellowship from the Japan Society for the Promotion of Science for Young Scientists.

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Authors and Affiliations

  1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka, 599-8531, Japan

    Takahide Fukuyama, Takashi Kippo, Kanako Hamaoka & Ilhyong Ryu

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  1. Takahide Fukuyama
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  2. Takashi Kippo
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  3. Kanako Hamaoka
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  4. Ilhyong Ryu
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Correspondence to Ilhyong Ryu.

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Br-Radical-Mediated [3+2] Annulation: Synthesis of 2-Bromomethyl-Substituted Alkenylcyclopentanes by the Reaction of Alkenylcyclopropanes with Allyl Bromides under Photo Irradiation

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Fukuyama, T., Kippo, T., Hamaoka, K. et al. Br-radical-mediated [3+2] annulation: synthesis of 2-bromomethyl-substituted alkenylcyclopentanes by the reaction of alkenylcyclopropanes with allyl bromides under photo irradiation. Sci. China Chem. 62, 1525–1528 (2019). https://doi.org/10.1007/s11426-019-9595-0

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  • DOI: https://doi.org/10.1007/s11426-019-9595-0

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