Three-Component Ruthenium-Catalyzed Direct Meta-Selective C–H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes

Multicomponent reactions are fundamentally different from two-component reactions, as multicomponent reactions can enable the efficient and step-economical construction of complex molecular scaffolds from simple precursors. Here, an unprecedented three-component direct C–H addition was achieved in t...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-09, Vol.141 (35), p.13914-13922
Main Authors: Wang, Xin-Gang, Li, Yuke, Liu, Hong-Chao, Zhang, Bo-Sheng, Gou, Xue-Ya, Wang, Qiang, Ma, Jun-Wei, Liang, Yong-Min
Format: Article
Language:English
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Summary:Multicomponent reactions are fundamentally different from two-component reactions, as multicomponent reactions can enable the efficient and step-economical construction of complex molecular scaffolds from simple precursors. Here, an unprecedented three-component direct C–H addition was achieved in the challenging meta-selective fashion. Fluoroalkyl halides and a wide range of alkenes, including vinylarenes, unactivated alkenes, and internal alkenes, were employed as the coupling partners of arenes in this strategy. The detailed mechanism presented is supported by kinetic isotope studies, radical clock experiments, and density functional theory calculations. Moreover, this strategy provided access to various fluoride-containing bioactive 1,1-diarylalkanes and other challenging synthetically potential products.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b06608