A Practical Lewis Base Catalyzed Electrophilic Chlorination of Arenes and Heterocycles

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• 作者：Sean M. Maddox ; Christopher J. Nalbandian ; Davis E. Smith ; Jeffrey L. Gustafson
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 20, 2015
• 年：2015
• 卷：17
• 期：4
• 页码：1042-1045
• 全文大小：353K
• ISSN：1523-7052

文摘

A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.