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Facile Access to Fluoroaromatic Molecules by Transition‐Metal‐Free C–F Bond Cleavage of Polyfluoroarenes: An Efficient, Green, and Sustainable Protocol
Author(s) -
Liu Cuibo,
Zhang Bin
Publication year - 2016
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201500248
Subject(s) - nucleophilic aromatic substitution , chemistry , bond cleavage , molecule , combinatorial chemistry , nucleophile , nucleophilic substitution , computational chemistry , organic chemistry , catalysis
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 (S N 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 S N 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 S N Ar reactions of polyfluoroarenes as well as our perspective on the future development of this chemistry.