Palladium-catalyzed highly regioselective and stereoselective arylation of electron-rich allylamines with aryl bromides
文献类型：期刊论文
| 作者 | Jiang, Zhen1; Zhang, Lingjuan1; Dong, Chaonan1; Ma, Baode2; Tang, Weijun3; Xu, Lijin1,2; Fan, Qinghua2; Xiao, Jianliang3 |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2012-06-17 |
| 卷号 | 68期号:24页码:4919-4926 |
| 关键词 | Heck Reaction Allylamine Arylation Palladium Regioselectivity |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2012.02.081 |
| 英文摘要 | A palladium-catalyzed, highly efficient Heck arylation of electron-rich N,N-diprotected allylamine derivatives with a wide range of aryl bromides under ligand-free conditions has been developed. In the presence of Pd(OAc)(2) and an appropriate additive, the reaction proceeds with excellent regioselectivity and stereoselectivity, leading exclusively to the gamma-arylated (E)-allylamine products in good to excellent yields. It was found that the choice of solvent, olefin, additive and temperature has an important influence on the reaction. Worthy of note is that good results were observed only when using N,N-diprotected allylamines containing carbamate moiety, and the steric properties of allylamines also have important impacts on the regiocontrol. The use of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or HQ (hydroquinone) as the additive is also crucial for securing a faster reaction rate. This method provides a straightforward approach for the efficient synthesis of various gamma-arylated, linear (E)-allylamines. (C) 2012 Elsevier Ltd. All rights reserved. |
| 语种 | 英语 |
| WOS记录号 | WOS:000304798800042 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/47565]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Xu, Lijin |
| 作者单位 | 1.Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China 2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China 3.Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England |
| 推荐引用方式 GB/T 7714 | Jiang, Zhen,Zhang, Lingjuan,Dong, Chaonan,et al. Palladium-catalyzed highly regioselective and stereoselective arylation of electron-rich allylamines with aryl bromides[J]. TETRAHEDRON,2012,68(24):4919-4926. |
| APA | Jiang, Zhen.,Zhang, Lingjuan.,Dong, Chaonan.,Ma, Baode.,Tang, Weijun.,...&Xiao, Jianliang.(2012).Palladium-catalyzed highly regioselective and stereoselective arylation of electron-rich allylamines with aryl bromides.TETRAHEDRON,68(24),4919-4926. |
| MLA | Jiang, Zhen,et al."Palladium-catalyzed highly regioselective and stereoselective arylation of electron-rich allylamines with aryl bromides".TETRAHEDRON 68.24(2012):4919-4926. |
入库方式： OAI收割
来源：化学研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。