Efficient copper(II)-catalyzed addition of activated methylene compounds to alkenes

Efficient copper(II)-catalyzed addition of activated methylene compounds to alkenes
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铜(II)催化活化亚甲基化合物与烯烃的高效加成

DOI:
10.1021/jo800836g
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发表时间:
2008-07-18
影响因子:
3.6
通讯作者:
Wu, Sizhong
Wu, Sizhong
中科院分区:
化学2区
文献类型:
--
作者:
Li, Yu;Yu, Zhengkun;Wu, Sizhong

文献摘要

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以三氟甲磺酸铜(II)为催化剂,实现了β-二酮与苯乙烯、异戊二烯、环烯醇醚和二烯的高效区域选择性加成反应。溶剂效应是突出的反应,和所需的加成产物得到良好的到优异的产率只有在二氧六环或离子液体[bmim] PF 6。该机制表明,三氟甲磺酸铜(II)激活β-二酮底物的烯醇O-H键,引发加成反应。
Efficient regioselective addition of beta-diketones to styrenes, norbornene, cyclic enol ether, and diene has been realized by means of copper(II) triflate as the catalyst. The solvent effect is prominent on the reactions, and the desired addition products were obtained in good to excellent yields only in dioxane or ionic liquid [bmim]PF6. The mechanism suggests that copper(II) triflate activates the enolic O-H bond of a beta-diketone substrate to initiate the addition reaction.