Organic Letters
Organic Letters
5 years ago

Frustrated Lewis Pair Catalyzed C–H Activation of Heteroarenes: A Stepwise Carbene Mechanism Due to Distance Effect

Frustrated Lewis Pair Catalyzed C–H Activation of Heteroarenes: A Stepwise Carbene Mechanism Due to Distance Effect
Yan Liu, Yinwu Li, Youxiang Shao, Zhuofeng Ke, Jianyu Zhang
This study presents new mechanistic insights into the frustrated Lewis pairs (FLPs) catalyzed C–H activation of heteroarenes. Besides the generally accepted concerted C–H activation, a novel stepwise carbene type pathway is proposed as an alternative mechanism. The reaction mechanisms can be varied by tuning the distance between Lewis acid and Lewis base due to catalyst–substrate match. These results should expand the understanding of the structure and function of FLPs for catalyzed C–H activation.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b00024

DOI: 10.1021/acs.orglett.8b00024

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