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Regiocontrolled Halogen Dance of Bromothiophenes and Bromofurans
Daichi Mari1, Naoki Miyagawa1, Kentaro Okano1
1Department of Chemical Science and Engineering , Kobe University , 1-1 Rokkodai , Nada, Kobe 657-8501 , Japan.
Abstract:
The LDA (lithium diisopropylamide)-promoted regiocontrolled halogen dance of α-bromothiophenes and α-bromofurans is described. Bromothiophenes bearing a diethyl acetal moiety undergo selective deprotonation at the β-position adjacent to the bromo group. In contrast, oxazoline, ester, and amide groups act as directing groups in the initial lithiation step to generate a carbanion at the β-position neighboring the directing group to exclusively give the other regioisomer. These results can be applied to the regiocontrolled halogen dance of bromofuran derivatives.
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