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

Authors :
Qiang Wang
Yuke Li
Hong-Chao Liu
Yong-Min Liang
Xin-Gang Wang
Xue-Ya Gou
Jun-Wei Ma
Bo-Sheng Zhang
Source :
Journal of the American Chemical Society. 141:13914-13922
Publication Year :
2019
Publisher :
American Chemical Society (ACS), 2019.

Abstract

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.

Details

ISSN :
15205126 and 00027863
Volume :
141
Database :
OpenAIRE
Journal :
Journal of the American Chemical Society
Accession number :
edsair.doi...........3adf81997da87f149198be21f60b4546