Palladium-Catalyzed N-Arylation of Cyclopropylamines

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• 作者：Peter G. Gildner ; Andrew DeAngelis ; Thomas J. Colacot
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：18
• 期：6
• 页码：1442-1445
• 全文大小：410K
• ISSN：1523-7052

文摘

A general method has been developed for the previously challenging arylation of cyclopropylamine and N-arylcyclopropylamines. Highly active, air-stable, and commercially available R-allylpalladium precatalysts provide access to a wide range of (hetero)arylated cyclopropylanilines in high yields. Precatalysts [(tBuBrettPhos)Pd(allyl)]OTf and [(BrettPhos)Pd(crotyl)]OTf, deliver monoarylated products, while (PtBu₃)Pd(crotyl)Cl is suited for preparing unsymmetrical diarylated products. The developed conditions tolerate a range of functional groups and heterocycles, allowing access to an array of arylated cyclopropylamines, a motif present in prominent drug molecules.