Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

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• 作者：Song Song ; Xiang Sun ; Xinwei Li ; Yizhi Yuan ; Ning Jiao
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：June 19, 2015
• 年：2015
• 卷：17
• 期：12
• 页码：2886-2889
• 全文大小：422K
• ISSN：1523-7052

文摘

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.