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Issue 13, 2018
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Controlled mono-olefination versus diolefination of arenes via C–H activation in water: a key role of catalysts

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Abstract

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.

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

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Publication details

The article was received on 10 Mar 2018, accepted on 12 Jun 2018 and first published on 13 Jun 2018


Article type: Paper
DOI: 10.1039/C8GC00790J
Citation: Green Chem., 2018,20, 3140-3146
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    Controlled mono-olefination versus diolefination of arenes via C–H activation in water: a key role of catalysts

    H. Zhang, Z. Yang, Q. Ma, J. Liu, Y. Zheng, M. Guan and Y. Wu, Green Chem., 2018, 20, 3140
    DOI: 10.1039/C8GC00790J

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