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学科主题: 金属有机化学
题名: Iron carbenoid-mediated ylide reactions
其他题名: 铁卡宾参与的叶立德反应
作者: Sun XL(孙秀丽) ; Zheng JC(郑君成) ; Tang Y(唐勇)
通讯作者: 唐勇
刊名: Pure Appl. Chem.
发表日期: 2010
卷: 82, 期:3, 页:625-634
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所
英文摘要: Electrophilic metal carbenoids, readily available from diazo compounds, prove to be good reagents for the preparation of ylides under neutral conditions. We have extended the strategy to synthesize allenes from diazoacetates with both stable and unstable ketenes in the presence of PPh3 and Fe(TCP)Cl (0.5 mol %), which provided an easy access to optically active 4,4-disubstituted allenic esters by employing enantiopure phosphines. The mechanism involving the generation of ylide through catalytic transfer of an iron(II) carbene to phosphine was confirmed. A tandem Wittig-Nazarov cyclization reaction was further developed based on these results, culminating in a straightforward method for the construction of beta-methylenecyclopentenones in a multistep one-pot manner without isolation of intermediates. By combining AsPh3 and iron carbenoids, a catalytic Wittig reaction in toluene/water biphasic system was accomplished, affording alpha,beta-unsaturated esters in high yields with E/Z above 50/1. Surprisingly, crotonate-derived phosphorus ylide reacted with electrophilic iron carbenoid, affording 1,1,4-trisubstituted 1,3-butadienes with high regio-and stereo-selectivities, where a new ylide generated via formal intermolecular carbenoid insertion into olefinic C-H bonds of the crotonate-derived phosphorus ylide was proposed.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000276000200013
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/19383
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:
Sun XL,Zheng JC,Tang Y. Iron carbenoid-mediated ylide reactions[J]. Pure Appl. Chem.,2010,82(3):625-634.
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