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SET-Induced Biaryl Cross-Coupling: An SRN1 Reaction

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journal contribution
posted on 17.12.2015, 01:09 by Brandon E. Haines, Olaf Wiest
The SET-induced biaryl cross-coupling reaction is established as the first example of a Grignard SRN1 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 MgPh2 radical anion intermediate. A new mechanism is proposed.

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