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学科主题: 金属有机化学
题名: Pd-Catalyzed Carbonylation of Diazo Compounds at Atmospheric Pressure: A Catalytic Approach to Ketenes
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
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)
通讯作者: 李玉学 ; 王剑波
刊名: J. Am. Chem. Soc.
发表日期: 2011
卷: 133, 期:12, 页:4330-4341
收录类别: SCI
部门归属: 北京大学; 中科院上海有机化学研究所
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.
语种: 英语
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WOS记录号: WOS:000291715300039
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/27897
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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Recommended Citation:
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.
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