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 Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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.

Original languageEnglish
Pages (from-to)1525-1528
Number of pages4
JournalScience China Chemistry
Volume62
Issue number11
DOIs
StatePublished - Nov 2019

Keywords

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

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