Long-range Effect of Bromine in the Deprotonative Metalation of Aromatic Compounds

Abstract

Deprotonative metalation has been largely used to functionalize aromatic compounds. The efficiency of such reactions, as well as their regioselectivity, depends on the substituents connected to the rings. In contrast with other groups such as fluorine and methoxy, bromine exhibits a long-range acidifying effect. Here we try to depict this particular effect of bromine through different examples in which deprotometalation takes place at a remote position.

Keywords

• Acidity
• Aromatic compounds
• Deprotonative metalation
• Long-range effects
• Substituent effects