arylzink

An aryl zinc compound is an organometallic compound where an aryl group is bonded to a zinc atom. These compounds are typically formed by the reaction of an aryl halide with zinc metal, often in the presence of a catalyst, or by the transmetallation of an aryl lithium or aryl Grignard reagent with a zinc halide. Aryl zinc compounds are generally less reactive than their organolithium or Grignard counterparts, which makes them more selective in certain chemical transformations.

One of the most significant applications of aryl zinc compounds is in cross-coupling reactions, such as the Negishi coupling. In this palladium-catalyzed reaction, an aryl zinc compound couples with an organic halide or pseudohalide to form a new carbon-carbon bond. This reaction is highly versatile and tolerates a wide range of functional groups, making it a powerful tool in organic synthesis for the construction of complex molecules, including pharmaceuticals and natural products.

The preparation of aryl zinc compounds often involves milder conditions compared to other organometallic reagents. They can be prepared directly from aryl halides using activated zinc or via halogen-metal exchange. The stability of aryl zinc reagents allows for their handling in air and moisture to some extent, although they are still best handled under inert atmosphere. Their reduced basicity and nucleophilicity compared to Grignard or organolithium reagents contribute to their improved functional group tolerance and chemoselectivity in reactions.