Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of alpha,alpha-Difluorohomoallylic Amines

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	Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of alpha,alpha-Difluorohomoallylic Amines
	Le XY(乐旭义) ; Qiu XL(邱小龙) ; Qing FL(卿凤翎)
刊名	Chin. J. Chem.
	2009
卷号	27 期号:1 页码:141-150
ISSN号	1001-604X
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
通讯作者	卿凤翎
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.
学科主题	氟化学 ; 金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/cjoc.200990007
语种	英语
WOS记录号	WOS:000264039400024
公开日期	2013-02-22
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/17657]
专题	上海有机化学研究所_中科院有机氟化学重点实验室
推荐引用方式 GB/T 7714	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.
APA	乐旭义,邱小龙,&卿凤翎.(2009).Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of alpha,alpha-Difluorohomoallylic Amines.Chin. J. Chem.,27(1),141-150.
MLA	乐旭义,et al."Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of alpha,alpha-Difluorohomoallylic Amines".Chin. J. Chem. 27.1(2009):141-150.