Rethinking carbanion chemistry from donor substituents to weakly coordinating carbanions.

Abstract

Carbanionic compounds provide unique reactivity patterns resulting from the high negative partial charge at the carbon centre, making them invaluable in chemical synthesis. They are important reagents in synthesis, including for challenging metalation reactions or the formation of C-C bonds. Despite this, broader applications have long been limited by their high reactivity and sensitivity to air and moisture. However, recent studies have underscored the versatility of carbanions beyond their traditional role as strong bases and nucleophiles. Utilization of molecular design strategies has opened applications such as their use as electron-donating groups isoelectronic with amines, ambiphilic reagents and even as weakly coordinating anions. In this review article, we provide an overview of these emerging uses of carbanionic compounds, aiming to inspire a broader rethinking of their potential and to encourage the development of new applications.