Affiliation:
1. Organization for Research Promotion, Osaka Metropolitan University (OMU)
2. Department of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU)
3. Research Division of Organic Materials, Osaka Research Institute of Industrial Science and Technology (ORIST)
Abstract
AbstractThe radical bromoallylation of alkynes, allenes, and vinylidene cyclopropanes proceeds efficiently in the presence of a radical initiator to give 2-bromo-substituted 1,4-, 1,5-, and 1,6-diene derivatives, respectively. Three-component reactions comprised of allenes, electron-deficient alkenes, and allyl bromides give 1,7-dienes in good yields. The bromoallylation of an arylalkene can override β-scission of the bromine radical from β-bromoalkyl radicals to give 5-bromoalkenes, whilst the bromoallylation of vinylcyclopropanes is accompanied by 5-exo ring closure to give 1-(bromomethyl)-2-vinylcyclopentane derivatives in good yields. All of the products contain a reactive vinyl bromide moiety, which can be readily functionalized by Pd-catalyzed cross-coupling and radical cascade reactions.1 Introduction2 Synthesis of 1,4-Dienes by Bromoallylation of Acetylenes3 Synthesis of 1,5-Dienes by Bromoallylation of Allenes4 Synthesis of 1,6-Dienes by Bromoallylation of Methylenecyclopropanes5 Synthesis of 1,7-Dienes by Bromoallylation of Allenes and Electron-Deficient Alkenes6 Bromoallylation of Arylalkenes and Vinylcyclopropanes7 Conclusion
Funder
Japan Society for the Promotion of Science
National Science and Technology Council
National Yang Ming Chiao Tung University
Cited by
2 articles.
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