Oxidative Addition and Reductive Elimination in the Gilman Reaction

Oxidative Addition and Reductive Elimination in the Gilman Reaction [Pg.572]

Some reactions of the Gilman reagent with an alkyl halide occur in two steps, not by an Sj 2 mechanism. A two-step sequence occurs when a dialkyl cuprate reacts with an alkyl iodide. [Pg.572]

Oxidative addition. In an oxidative addition reaction, the oxidation state of the transition metal, copper(I) in a Gilman reagent, changes to copper(III). [Pg.572]

Reductive elimination. The second step of the reaction is reductive elimination. In this step, the initial adduct rearranges to give a new carbon-carbon bond. [Pg.572]

The above reaction is an example of coupling reaction of a Gilman dialkylcuprate and a vinyl halide. The reaction replaces iodide with a methyl group. A Grignard reagent could not be used without first protecting the alcohol group, [Pg.573]