Pd-Catalyzed Carbonylation of Diazo Compounds at Atmospheric Pressure: A Catalytic Approach to Ketenes
文献类型：期刊论文
| 作者 | ZHANG ZHENHUA ; LIU YIYANG ; Ling L(凌琳) ; Li YX(李玉学) ; DONG YIAN ; GONG MINGXING ; ZHAO XIAOKUN ; Zhang Y(张艳) ; Wang JB(王剑波) |
| 刊名 | J. Am. Chem. Soc.
 |
| 出版日期 | 2011 |
| 卷号 | 133期号:12页码:4330-4341 |
| ISSN号 | 0002-7863 |
| 其他题名 | 常压下Pd催化的重氮化合物的羰基化: 得到烯酮的催化途径 |
| 通讯作者 | 李玉学 ; 王剑波 |
| 英文摘要 | The carbonylation of carbenes through catalytic cycles is highly desirable due to the importance of ketene-mediated reactions in organic synthesis. In this investigation, a highly efficient and mild catalytic approach toward ketene intermediates has been developed based on Pd-catalyzed carbonylation of diazo compounds with CO. When alpha-diazocarbonyl compounds or N-tosylhydrazone salts are heated in the presence of a palladium catalyst under atmospheric pressure of CO, ketene intermediates are formed in situ, where they undergo further reactions with various nucleophiles such as alcohols, amines, or imines. The Pd-catalyzed tandem carbonylation-Staudinger cycloaddition gives beta-lactam derivatives in good yields with excellent trans diastereoselectivity. The results from DFT calculation on the reaction mechanism suggest that Pd is involved in the [2 + 2] cycloaddition process and affects the diastereoselectivity of the beta-lactam products by assisting isomerization of the addition intermediate. On the other hand, the acylketenes generated from the Pd-catalyzed carbonylation of alpha-diazoketones react with imines in a formal [4 + 2] cycloaddition manner to afford 1,3-dioxin-4-one derivatives. This straightforward carbonylation provides a new approach toward highly efficient catalytic generation of ketene species under mild conditions. |
| 学科主题 | 金属有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/ja107351d |
| 语种 | 英语 |
| WOS记录号 | WOS:000291715300039 |
| 公开日期 | 2013-08-22 |
| 源URL | [http://202.127.28.38/handle/331003/27897]  |
| 专题 | 上海有机化学研究所_金属有机化学国家重点实验室 |
| 推荐引用方式 GB/T 7714 | ZHANG ZHENHUA,LIU YIYANG,Ling L,et al. Pd-Catalyzed Carbonylation of Diazo Compounds at Atmospheric Pressure: A Catalytic Approach to Ketenes[J]. J. Am. Chem. Soc.,2011,133(12):4330-4341. |
| APA | ZHANG ZHENHUA.,LIU YIYANG.,凌琳.,李玉学.,DONG YIAN.,...&王剑波.(2011).Pd-Catalyzed Carbonylation of Diazo Compounds at Atmospheric Pressure: A Catalytic Approach to Ketenes.J. Am. Chem. Soc.,133(12),4330-4341. |
| MLA | ZHANG ZHENHUA,et al."Pd-Catalyzed Carbonylation of Diazo Compounds at Atmospheric Pressure: A Catalytic Approach to Ketenes".J. Am. Chem. Soc. 133.12(2011):4330-4341. |
入库方式： OAI收割
来源：上海有机化学研究所
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