Rhodium(III)-Catalyzed Regioselective Direct C-2 Alkenylation of Indoles Assisted by the Removable N-(2-Pyrimidyl) Group
文献类型：期刊论文
| 作者 | Gong, Binwei2,3; Shi, Jingjing3 ; Wang, Xiaowei2,3; Yan, Yunnan3,5; Li, Qiu3,4; Meng, Yanqiu2; Xu, H. Eric1,3; Yi, Wei3
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| 刊名 | ADVANCED SYNTHESIS & CATALYSIS
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| 出版日期 | 2014-01-13 |
| 卷号 | 356期号:1页码:137-143 |
| 关键词 | acrylates C-2 alkenylation indoles N-(2-pyrimidyl) group rhodium(III) catalysts |
| ISSN号 | 1615-4150 |
| DOI | 10.1002/adsc.201300700 |
| 文献子类 | Article |
| 英文摘要 | The C-2-alkenylindole unit is a key component of numerous natural products and pharmacophores. However, the intermolecular direct construction of the core structural motif remains challenging in organic synthesis. Here we report a new, efficient, and versatile methodology for the synthesis of C-2-alkenylindoles through rhodium(III)-catalyzed direct CH functionalization of indoles with acrylates under air by employing a metal-directing group strategy. This strategy gives a rare selectivity for the alkenylation N-(2-pyrimidyl)indoles at the C-2 position and provides the functionalized C-2- alkenylindoles under mild conditions with broad substrate tolerance. An expansion of the methodology has also been demonstrated to, for example, the direct alkenylation of pyrrole and facile deprotection of the pyrimidyl group. All the results suggest that this methodology could be served as a highly attractive alternative for the direct construction of biologically important C-2-alkenylindoles. |
| WOS关键词 | C-H FUNCTIONALIZATION ; BOND ACTIVATION ; VERSATILE SYNTHESIS ; RHODIUM CATALYSIS ; ALKYNES ; EFFICIENT ; PYRROLES ; C2-ALKENYLATION ; BENZAMIDES ; ACID |
| 资助项目 | Jay and Betty Van Andel Foundation[00000000] ; Amway (China)[00000000] ; Chinese Postdoctoral Science Foundation[2012MM511158] ; Chinese Postdoctoral Science Foundation[2013T60477] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000331059200006 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/277231]  |
| 专题 | 药物靶标结构与功能中心 |
| 通讯作者 | Xu, H. Eric |
| 作者单位 | 1.Van Andel Res Inst, Program Struct Biol & Drug Discovery, Lab Struct Sci, Grand Rapids, MI 49503 USA 2.Shenyang Univ Chem Technol, Coll Pharmaceut & Biol Engn, Shenyang 110142, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, VARI SIMM Ctr,Ctr Struct & Funct Drug Targets, Shanghai 201203, Peoples R China; 4.Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Jiangsu, Peoples R China; 5.Gannan Med Univ, Coll Pharmaceut Sci, Ganzhou 341000, Jiangxi, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Gong, Binwei,Shi, Jingjing,Wang, Xiaowei,et al. Rhodium(III)-Catalyzed Regioselective Direct C-2 Alkenylation of Indoles Assisted by the Removable N-(2-Pyrimidyl) Group[J]. ADVANCED SYNTHESIS & CATALYSIS,2014,356(1):137-143. |
| APA | Gong, Binwei.,Shi, Jingjing.,Wang, Xiaowei.,Yan, Yunnan.,Li, Qiu.,...&Yi, Wei.(2014).Rhodium(III)-Catalyzed Regioselective Direct C-2 Alkenylation of Indoles Assisted by the Removable N-(2-Pyrimidyl) Group.ADVANCED SYNTHESIS & CATALYSIS,356(1),137-143. |
| MLA | Gong, Binwei,et al."Rhodium(III)-Catalyzed Regioselective Direct C-2 Alkenylation of Indoles Assisted by the Removable N-(2-Pyrimidyl) Group".ADVANCED SYNTHESIS & CATALYSIS 356.1(2014):137-143. |
入库方式： OAI收割
来源：上海药物研究所
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