title: SET-induced biaryl cross-coupling: an S(RN)1 reaction.
abstract: The SET-induced biaryl cross-coupling reaction is established as the first example of a Grignard S(RN)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 MgPh2 radical anion intermediate. A new mechanism is proposed.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame , Notre Dame, Indiana 46556, United States.
authors.forename: Brandon E
authors.initials: BE
authors.lastname: Haines
authors.forename: Olaf
authors.initials: O
authors.lastname: Wiest
mesh_terms: D002384:Catalysis; D007477:Ions / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D007477:Ions; D058116:Lewis Acids; D009942:Organometallic Compounds; D008274:Magnesium