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Science China Chemistry

, Volume 62, Issue 11, pp 1525–1528 | Cite as

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

  • Takahide Fukuyama
  • Takashi Kippo
  • Kanako Hamaoka
  • Ilhyong RyuEmail author
Articles
  • 53 Downloads

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.

Keywords

[3+2] annulation bromine radical alkenylcyclopropanes alkenylcyclopentanes photo irradiation 

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Notes

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.

Conflict of interest The authors declare that they have no conflict of interest.

Supplementary material

11426_2019_9595_MOESM1_ESM.pdf (2.8 mb)
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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Copyright information

© Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Takahide Fukuyama
    • 1
  • Takashi Kippo
    • 1
  • Kanako Hamaoka
    • 1
  • Ilhyong Ryu
    • 1
    Email author
  1. 1.Department of Chemistry, Graduate School of ScienceOsaka Prefecture UniversitySakai, OsakaJapan

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