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学科主题: 氟化学 ; 金属有机化学
题名: Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of alpha,alpha-Difluorohomoallylic Amines
其他题名: 金属存在下对N-乙酰化腙的二氟烯丙基化反应:高效制备二氟高烯丙基胺
作者: Le XY(乐旭义) ; Qiu XL(邱小龙) ; Qing FL(卿凤翎)
通讯作者: 卿凤翎
刊名: Chin. J. Chem.
发表日期: 2009
卷: 27, 期:1, 页:141-150
收录类别: SCI
部门归属: 上海有机所; 东华大学
英文摘要: Indium-mediated gem-difluoroallylation of aldehyde-derived N-acylhydrazones 1a-1q and 4a-4g with 3-bromo-3,3-difluoropropene 2 afforded alpha,alpha-difluorohomoallylic hydrazides 3a-3q and 5a-5g in high yields, respectively. Functional groups Such as nitro, phenolic hydroxyl, benzyloxy and even C=C bonds of alpha,beta-unsaturated aldehydes were compatible under this mild and operationally simple gem-difluoroallylic reaction condition. By means Of substitution of Zn powder for indium, gem-difluoroallylation of ketone-derived N-acylhydrazones 6a-6d also provided the corresponding alpha,alpha-difluorohomoallylic hydrazides 7a-7d in medium yields. The N-N bond cleavage of the hydrazide 3a proceeded smoothly to give the corresponding primary gem-difluorohomoallylic amine 8, which could be converted to gem-difluoro-delta-substituted alpha,beta-unsaturated lactam 11 via acryloylation followed by ring closing metathesis (RCM) reaction.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000264039400024
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17657
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Le XY,Qiu XL,Qing FL. Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of alpha,alpha-Difluorohomoallylic Amines[J]. Chin. J. Chem.,2009,27(1):141-150.
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