Palau鈥檆hlor: A Practical and Reactive Chlorinating Reagent

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• 作者：Rodrigo A. Rodriguez ; Chung-Mao Pan ; Yuki Yabe ; Yu Kawamata ; Martin D. Eastgate ; Phil S. Baran
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：May 14, 2014
• 年：2014
• 卷：136
• 期：19
• 页码：6908-6911
• 全文大小：415K
• 年卷期：v.136,no.19(May 14, 2014)
• ISSN：1520-5126

文摘

Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or 鈥淧alau鈥檆hlor鈥? inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated 蟺-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.