An efficient new methodology for the synthesis of 1-functionalized 2-halo-2-alkenes via hydrohalogenation reaction of electron-deficient allenes

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	An efficient new methodology for the synthesis of 1-functionalized 2-halo-2-alkenes via hydrohalogenation reaction of electron-deficient allenes
	Ma SM(麻生明) ; Li LT(李林涛)
刊名	Synlett
	2001
期号	8 页码:1206-1213
ISSN号	0936-5214
其他题名	通过缺电子联烯的氢卤化反应高效合成1－官能团2－卤代－1－烯烃
通讯作者	麻生明
英文摘要	The hydrohalogenation reactions of electron-deficient allenes, such as 1,2-allenic ketones, carboxylic acids, esters, amides, nitriles, sulfoxides(with the use of AlX^3/H^2O), sulfones, and phosphine oxides with MX(X=I,Br, Cl, M=Na,Li) in different solvents, such as HOAc, CF^3COOH-HOAc(1:1), CF^3COOH and THF were studied. The reaction is nucleophilic conjugate addition in nature and provides efficient entries to 1-functionalized 2-halo-2-alkenes. The β，γ－over α，β-selectivity and stereoselectivity depend on the solvent(s) and the temperature applied . In most cases, the Z-and E-isomers can be easily separated with chromatography on silicagel. The subsequent cross coupling reaction with organometallic reagents and terminal alkynes showed the synthetic potential of these products.
学科主题	有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1055/s-2001-16032
语种	英语
WOS记录号	WOS:000170344200003
公开日期	2013-01-15
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/11840]
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	Ma SM,Li LT. An efficient new methodology for the synthesis of 1-functionalized 2-halo-2-alkenes via hydrohalogenation reaction of electron-deficient allenes[J]. Synlett,2001(8):1206-1213.
APA	麻生明,&李林涛.(2001).An efficient new methodology for the synthesis of 1-functionalized 2-halo-2-alkenes via hydrohalogenation reaction of electron-deficient allenes.Synlett(8),1206-1213.
MLA	麻生明,et al."An efficient new methodology for the synthesis of 1-functionalized 2-halo-2-alkenes via hydrohalogenation reaction of electron-deficient allenes".Synlett .8(2001):1206-1213.