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Synthesis 2011(2): 207-209  
DOI: 10.1055/s-0030-1258350
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient and Regioselective Monobromination of Electron-Rich Aromatic Compounds Using Catalytic Hypervalent Iodine(III) Reagent

Zhongshi Zhou*a, Xuehan Heb
a College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, Zhejiang, P. R. of China
Fax: +86(571)88297172; e-Mail: zhoushan@hz.zj.cn;
b Zhejiang Institute of Geology and Mineral Resource Laboratory, Hangzhou 310007, Zhejiang, P. R. of China
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Publication History

Received 24 September 2010
Publication Date:
03 December 2010 (online)

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Abstract

An efficient and regioselective monobromination of electron-rich aromatic compounds is reported in which iodobenzene is used as the recyclable catalyst in combination with m-chloroperbenzoic acid as the terminal oxidant. The bromination of electron-rich aromatic compounds with lithium bromide was fast in tetrahydrofuran at room temperature, providing regioselective monobrominated products in good yields.

Key words

monobromination - hypervalent iodine reagent - catalytic oxidation

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