Controlled mono-olefination versus diolefination of arenes via C–H activation in water: a key role of catalysts,Green Chemistry

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Controlled mono-olefination versus diolefination of arenes via C–H activation in water: a key role of catalysts
Green Chemistry ( IF 9.3 ) Pub Date : 2018-06-13 , DOI: 10.1039/c8gc00790j
Hailong Zhang _{1,

2,

3,

4} , Zhongzhen Yang _{1,

2,

3,

4} , Qiang Ma _{1,

2,

3,

4} , Jinxin Liu _{1,

2,

3,

4} , Yang Zheng _{1,

2,

3,

4} , Mei Guan _{4,

5,

6,

7} , Yong Wu _{1,

2,

3,

4}

Affiliation

Herein, we report the olefination of arenes via C–H activation in water instead of in expensive and pollution-causing organic solvents. In this process, the catalysts were shown to play a key role in controlling mono- and diolefinations. More specifically, [Ru(p-cymene)Cl₂]₂ predominantly gave mono-olefinated products while [Cp*RhCl₂]₂ selectively afforded diolefinated products. Importantly, only relatively small amounts of the catalysts were required ([Ru(p-cymene)Cl₂]₂ 5 mol%, [Cp*RhCl₂]₂ 1 mol%) and the reaction time was significantly shortened from tens of hours using previous strategies to tens of minutes. Additionally, the new methodology was shown to work with a variety of functional groups and olefins, to achieve moderate to good yields of products, and to be applicable to a gram-scale synthesis at a low catalyst loading.

中文翻译：

在水中通过C–H活化控制芳烃的单烯烃与二烯烃的加成：催化剂的关键作用

在本文中，我们报告了在水中而不是在昂贵且造成污染的有机溶剂中通过C–H活化进行芳烃的烯化反应。在该方法中，显示出催化剂在控制单烯烃和二烯烃中起关键作用。更具体地，[Ru（对-cymene）Cl ₂ ] ₂主要产生单烯烃化产物，而[Cp * RhCl ₂ ] ₂选择性地提供二烯烃化产物。重要的是，仅需要相对少量的催化剂（[Ru（对-cymene）Cl ₂ ] ₂ 5 mol％，[Cp * RhCl ₂ ] ₂1 mol％），反应时间从使用先前策略的数十小时显着缩短至数十分钟。另外，该新方法已显示可与多种官能团和烯烃一起使用，以实现中等至良好的产物收率，并适用于低催化剂负载下的克级合成。

更新日期：2018-07-02

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