Indirect ortho Functionalization of Substituted Toluenes through ortho Olefination of N,N-Dimethylbenzylamines Tuned by the Acidity of Reaction Conditions

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• 作者：Guixin Cai ; Ye Fu ; Yizhou Li ; Xiaobing Wan ; Zhangjie Shi
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：June 20, 2007
• 年：2007
• 卷：129
• 期：24
• 页码：7666 - 7673
• 全文大小：212K
• 年卷期：v.129,no.24(June 20, 2007)
• ISSN：1520-5126

文摘

Highly regioselective olefination of substituted N,N-dimethylbenzylamines was developed by tuningthe acidity of reaction conditions based on analysis of their features. The ortho-functionalized N,N-dimethylbenzylamines were further transformed into 3-(2'-tolyl)propanoic acid and its derivatives undermild conditions. These two transformations could be combined into one pot, and 3-(2'-tolyl)propanoic acidand its derivatives were obtained in moderate to good yields. Mechanistic studies indicated that electrophilicattack on the phenyl ring by the Pd(II) ion assisted by the N,N-dimethylaminomethyl group was a key stepduring this catalytic transformation, which was controlled by the acidity of the reaction conditions.