Using 1,4-dipolar-aryne cycloaddition methodology, a convenient, short
synthesis of several fluoroanthraquinones is presented which involves
the reaction of haloarenes and 3-cyanophthalides in the presence of l
ithium diisopropylamide (LDA) in tetrahydrofuran (THF). The fluorine s
ubstituent(s) can be introduced by using fluorine-substituted haloaren
es and/or 3-cyanophthalides. Similarly, fluorine-substituted pyridines
can be prepared by treating fluorine-substituted cyanophthalides and
halopyridines in the presence of lithium diisopropylamide.