Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination
文献类型：期刊论文
| 作者 | Liu, H ; Li, CL ; Qiu, D ; Tong, XF |
| 刊名 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
 |
| 出版日期 | 2011 |
| 卷号 | 133期号:16页码:6187 |
| 关键词 | CROSS-COUPLING REACTIONS ARYLPALLADIUM(II) HALIDE-COMPLEXES RADICAL CYCLIZATION REACTIONS ARYL HALIDES BOND FORMATION CARBON-MONOXIDE OXIDATIVE ADDITION HALOGEN EXCHANGE STEREOSELECTIVE-SYNTHESIS HECK REACTION |
| ISSN号 | 0002-7863 |
| 通讯作者 | Qiu, D (reprint author), Chinese Acad Sci ICCAS, Beijing Natl Lab Mol Sci, State Key Lab Polymer Phys & Chem, Inst Chem, Beijing 100190, Peoples R China. |
| 中文摘要 | A palladium-catalyzed iodine atom transfer cycloisomerization of (Z)-1-iodo-1,6-diene has been developed, which provides a facile method to construct six-memebered heterocycles bearing an alkyl iodide group. The ligand screening shows that both the type and the quantity of ligand impose significant influences on this transformation, and the combination of 30 mol % 1,1'-bis(diphenylphosphino)ferrocene (DPPF) and 10 mol % Pd(OAc)(2) is the optimal choice. The catalytic cycle, consisting of oxidative addition of Pd(0) to vinyl iodide, intramolecular alkene insertion, and alkyl iodide reductive elimination, has been proposed and eventually supported by convincing evidence from a series of control experiments. More importantly, these control experiments disclose some features of the event of alkyl iodide reductive elimination: (1) this reductive elimination is proved to be a stereospecific process; and (2) both alkyl iodide oxidative addition and reductive elimination are not effected by a TEMPO additive. Besides its ability to undergo oxidative addition, the catalyst (palladium + DPPF) could also promote a radical transfer process. The findings described in this paper will be helpful for further development of the metal-catalyzed formation of a carbon-halide bond. |
| 收录类别 | SCI |
| 资助信息 | Shanghai Municipal Committee of Science and Technology [09ZR1408500]; Fundamental Research Funds for the Central Universities |
| 语种 | 英语 |
| 公开日期 | 2013-09-24 |
| 源URL | [http://ir.iphy.ac.cn/handle/311004/50561]  |
| 专题 | 物理研究所_物理所公开发表论文_物理所公开发表论文_期刊论文 |
| 推荐引用方式 GB/T 7714 | Liu, H,Li, CL,Qiu, D,et al. Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2011,133(16):6187. |
| APA | Liu, H,Li, CL,Qiu, D,&Tong, XF.(2011).Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,133(16),6187. |
| MLA | Liu, H,et al."Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 133.16(2011):6187. |
入库方式： OAI收割
来源：物理研究所
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