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学科主题: 金属有机化学
题名: Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols
其他题名: 铜催化下分子内烯基溴与醇偶联反应中4-exo环合的优先
作者: Fang YW(方烨汶) ; Li CZ(李超忠)
通讯作者: 李超忠
刊名: J. Am. Chem. Soc.
发表日期: 2007
卷: 129, 期:26, 页:8092-8093
收录类别: SCI
部门归属: 上海有机化学研究所
英文摘要: The copper-catalyzed intramolecular O-vinylation of gamma-bromohomoallylic alcohols was investigated. With 10 mol % of CuI as the catalyst and 20 mol % of 1,10-phenanthroline as the ligand, the reactions of 3-bromo-3-buten-1-ols in refluxing CH3CN led to the convenient formation of the corresponding 2-methyleneoxetanes in good to excellent yields via a 4-exo ring closure. The configuration of the CC bond was nicely retained. This methodology was then successfully extended to the cyclization in 5-exo, 6-exo, and even 6-endo modes. Moreover, the competition experiments revealed that 4-exo cyclization is fundamentally preferred over other modes of cyclization. On the other hand, the corresponding Pd(0)-catalyzed O-vinylation showed the predominance of 5-exo over 4-exo cyclization.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000247563700021
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/22828
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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Recommended Citation:
Fang YW,Li CZ. Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols[J]. J. Am. Chem. Soc.,2007,129(26):8092-8093.
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