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Rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift: Reaction scope and mechanism
其他题名铑催化的1,6烯炔环异构化-分子内卤素转移反应
Tong XF(童晓峰); Li D(李到); Zhang ZG(张兆国); Zhang XM(张绪穆)
2004
发表期刊J. Am. Chem. Soc.
ISSN0002-7863
卷号126期号:24页码:7601-7607
摘要The rhodium(1)-species-catalyzed cycloisomerization reaction of a wide spectrum of 1,6-enynes with an unusual intramolecular halogen shift was investigated. This Rh-catalyzed enyne cyclization reaction represents a new process for the synthesis of stereodefined alpha-halomethylene-gamma-butyrolactones, lactams, tetrahydrofurans, pyrrolidines, and cyclopentanes. Coordinatively unsaturated rhodium species ([Rh(COD)Cl](2) + dppb + AgSbF6) only catalyzes the reaction with enyne substrates bearing a Z-form double bond, while neutral rhodium species (RhCl(PPh3)(3)) Could catalyze enyne substrates bearing a Z- or E-form double bond to form the desired products and has a wider substrate scopes. The mechanism of the reaction was studied by the employment of control experiments with different enyne isomers, and a pi-allyl rhodium intermediate was suggested to explain the formation of the cyclic products with an intramolecular halogen shift.
学科领域金属有机化学
部门归属中国科学院上海有机化学研究所金属有机化学实验室; 美国宾州大学
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收录类别SCI
语种英语
WOS记录号WOS:000222120900041
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被引频次:58[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/27583
专题上海有机化学研究所
通讯作者Zhang ZG(张兆国)
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GB/T 7714
Tong XF,Li D,Zhang ZG,et al. Rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift: Reaction scope and mechanism[J]. J. Am. Chem. Soc.,2004,126(24):7601-7607.
APA 童晓峰,李到,张兆国,&张绪穆.(2004).Rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift: Reaction scope and mechanism.J. Am. Chem. Soc.,126(24),7601-7607.
MLA 童晓峰,et al."Rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift: Reaction scope and mechanism".J. Am. Chem. Soc. 126.24(2004):7601-7607.
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