Regioselective radical bromoallylation of allenes leading to 2-bromo-substituted 1,5-dienes

Takashi Kippo, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

The regioselective radical bromoallylation of allenes proceeded efficiently in the presence of AIBN as a radical initiator to give 2-bromo-substituted 1,5-dienes in excellent yields. The addition of a bromine radical took place regioselectively onto the central carbon of allenes generating a stable allyl radical, which underwent addition/β-fragmentation reactions with allylbromides. The products could be further functionalized by Pd-catalyzed coupling reactions.

Original languageEnglish
Pages (from-to)3864-3867
Number of pages4
JournalOrganic Letters
Volume13
Issue number15
DOIs
StatePublished - 5 Aug 2011

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