Subscribe to RSS
Directed Regioselective 2,5- and 3,5-Dimagnesiations of Substituted Arenes
Directed ortho-meta′- and meta-meta′-Dimetalations: A Template Base Approach to Deprotonation.
19 January 2015 (online)
The regioselective deprotonation of a directing group substituted arene substrate generally takes place in the ortho position, adjacent to the substituent. The authors developed a protocol by which the metalating agent deprotonates the arene at the more distant arene sites. Depending on the nature of the directing group, 2,5- or 3,5-dimetalation is observed. The dimagnesiated species were quenched with electrophiles.
Interestingly, the used disodium monomagnesium alkylamide forms a template that is responsible for the metalation at the more distant arene sites. The next challenge is the rational design of a range of template bases.