Facile Access to Fluoroaromatic Molecules by Transition-Metal-Free C-F Bond Cleavage of Polyfluoroarenes: An Efficient, Green, and Sustainable Protocol

Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]
Cuibo Liu, Bin Zhang

Abstract

The creation of new bonds via C-F bond cleavage of polyfluoroarenes has proven to be an important and powerful tool in synthetic chemistry. Using such a strategy, a myriad of valuable partially fluoroaromatic molecules and building blocks can be obtained. The transition-metal-free nucleophilic aromatic substitution (SN Ar) strategy has aroused the continuing interest of researchers due to its simple, mild, economical, and environmentally benign characteristics, which have been successfully applied to C-F bond functionalizations. In this account, we present a summary of the recent investigations of polyfluoroarenes involving SN Ar reactions and discuss some of our recent endeavors in the construction of partially fluoroaromatic molecules. Through this strategy, many new bonds including C-C, C-N, C-O, C-S, and C-H bonds can be created. Additionally, brief discussions on the transformation mechanisms are also provided. Finally, we discuss the existing limitations of the SN Ar reactions of polyfluoroarenes as well as our perspective on the future development of this chemistry.

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Citations

Mar 10, 2020·Chemistry : a European Journal·Koichi OkamotoHideki Yorimitsu
Mar 28, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Òscar TorresPhilipp Wittwer
Dec 19, 2018·The Journal of Organic Chemistry·Rashmi SemwalSubbarayappa Adimurthy

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