Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions
文献类型：期刊论文
| 作者 | Cai, Guixin; Fu, Ye; Li, Yizhou; Wan, Xiaobing; Shi, Zhangjie |
| 刊名 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
 |
| 出版日期 | 2007-06-20 |
| 卷号 | 129期号:24页码:7666-7673 |
| ISSN号 | 0002-7863 |
| DOI | 10.1021/ja070588a |
| 英文摘要 | Highly regioselective olefination of substituted N,N-dimethylbenzylamines was developed by tuning the 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 under mild conditions. These two transformations could be combined into one pot, and 3-(2'-tolyl)propanoic acid and its derivatives were obtained in moderate to good yields. Mechanistic studies indicated that electrophilic attack on the phenyl ring by the Pd(II) ion assisted by the N,N-dimethylaminomethyl group was a key step during this catalytic transformation, which was controlled by the acidity of the reaction conditions. |
| 语种 | 英语 |
| WOS记录号 | WOS:000247240500038 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/61749]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Shi, Zhangjie |
| 作者单位 | 1.Peking Univ, BNLMS, PKU Green Chem Ctr, Coll Chem, Beijing 100871, Peoples R China 2.Peking Univ, Coll Chem, Key Lab Biooorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China 3.E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China |
| 推荐引用方式 GB/T 7714 | Cai, Guixin,Fu, Ye,Li, Yizhou,et al. Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2007,129(24):7666-7673. |
| APA | Cai, Guixin,Fu, Ye,Li, Yizhou,Wan, Xiaobing,&Shi, Zhangjie.(2007).Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,129(24),7666-7673. |
| MLA | Cai, Guixin,et al."Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 129.24(2007):7666-7673. |
入库方式： OAI收割
来源：化学研究所
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