SET-Induced Biaryl Cross-Coupling:
An S<sub>RN</sub>1 Reaction
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Abstract
The
SET-induced biaryl cross-coupling reaction is established as
the first example of a Grignard S<sub>RN</sub>1 reaction. The reaction
is examined within the mechanistic framework of dissociative electron
transfer in the presence of a Lewis acid. DFT calculations show that
the reaction proceeds through a radical intermediate in the form of
an Mg ion-radical cage, which eludes detection in trapping experiments
by reacting quickly to form an MgPh<sub>2</sub> radical anion intermediate.
A new mechanism is proposed
