CuO/SiO2 as a simple, effective and recoverable catalyst for alkylation of indole derivatives with diazo compounds
CuO/SiO2 as a simple, effective and recoverable catalyst for alkylation of indole derivatives with diazo compounds
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DOI：
10.1039/c3ob40264a
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发表时间：
2013-01-01
影响因子：
3.2
通讯作者：
Zaccheria, Federica
中科院分区：
文献类型：
--
作者：
Fraile, Jose M.;Le Jeune, Karel;Zaccheria, Federica
在温和的反应条件下，二氧化硅上的纯无机氧化铜催化苯基重氮基乙酸甲酯与N-甲基吲哚的反应，在3位上进行烷基化（形式上为C-H插入），并且催化剂可以回收并至少连续重复使用5次，活性仅略有损失。反应的范围包括各种重氮化合物和吲哚或吡咯衍生物，导致烷基化或环丙烷化，这取决于杂环结构。一种替代机制，没有减少Cu（II）的Cu（I），提出了所获得的结果的基础上。
The purely inorganic copper oxide on silica catalyzes the reaction of methyl phenyldiazoacetate with N-methyl indole under mild reaction conditions, giving the alkylation (formally a C-H insertion) in position 3, and the catalyst can be recovered and reused at least in 5 consecutive runs with only minor loss in activity. The scope of the reaction includes various diazo compounds and indole or pyrrole derivatives leading to alkylation or cyclopropanation depending on the heterocycle structure. An alternative mechanism, without reduction of Cu(II) to Cu(I), is proposed on the basis of the obtained results.