Pd(II)-Catalyzed ortho-C–H Olefination/Dearomatization of N-Aryl Ureas: An Approach to Imine Derivatives

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• 作者：Pingping Jiang ; Yongbao Xu ; Fuxing Sun ; Xufei Liu ; Feng Li ; Renfu Yu ; Yang Li ; Qifeng Wang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：18
• 期：6
• 页码：1426-1429
• 全文大小：342K
• ISSN：1523-7052

文摘

An unprecedented approach for the synthesis of imine derivatives was achieved via a Pd(II)-catalyzed dearomatization reaction of N-aryl ureas with internal alkynes. The corresponding spirocyclic imine derivatives were obtained with 20 examples in good to excellent yields. Mechanistic investigation indicated that an interesting 1,3-palladium migration process led to the α-regioselective dearomatization when 2-naphthyl ureas were used as the substrates. Fused ring products could also be obtained to further prove this migration process.