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, Hui2,3; Li, Chaolong2,3; Qiu, Dong1; Tong, Xiaofeng2,3 |
| 刊名 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
 |
| 出版日期 | 2011-04-27 |
| 卷号 | 133期号:16页码:6187-6193 |
| ISSN号 | 0002-7863 |
| DOI | 10.1021/ja201204g |
| 英文摘要 | 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. |
| 语种 | 英语 |
| WOS记录号 | WOS:000292715500022 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/71587]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Qiu, Dong |
| 作者单位 | 1.Chinese Acad Sci ICCAS, Beijing Natl Lab Mol Sci, State Key Lab Polymer Phys & Chem, Inst Chem, Beijing 100190, Peoples R China 2.E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China 3.E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Hui,Li, Chaolong,Qiu, Dong,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):6187-6193. |
| APA | Liu, Hui,Li, Chaolong,Qiu, Dong,&Tong, Xiaofeng.(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),6187-6193. |
| MLA | Liu, Hui,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):6187-6193. |
入库方式： OAI收割
来源：化学研究所
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