Regioselective Radical Bromoallylation of Allenes Leading to 2-Bromo-Substituted 1,5-Dienes

Regioselective Radical Bromoallylation of Allenes Leading to 2-Bromo-Substituted 1,5-Dienes

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...

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Veröffentlicht in:Organic letters 2011-08, Vol.13 (15), p.3864-3867
Hauptverfasser: Kippo, Takashi, Fukuyama, Takahide, Ryu, Ilhyong
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container_title Organic letters
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creator Kippo, Takashi
Fukuyama, Takahide
Ryu, Ilhyong
description 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.
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title Regioselective Radical Bromoallylation of Allenes Leading to 2-Bromo-Substituted 1,5-Dienes
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