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
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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. |
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