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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 :
Wang XG
Li Y
Liu HC
Zhang BS
Gou XY
Wang Q
Ma JW
Liang YM
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2019 Sep 04; Vol. 141 (35), pp. 13914-13922. Date of Electronic Publication: 2019 Aug 20.
Publication Year :
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

Language :
English
ISSN :
1520-5126
Volume :
141
Issue :
35
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
31394035
Full Text :
https://doi.org/10.1021/jacs.9b06608