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Synfacts 2015; 11(2): 0183
DOI: 10.1055/s-0034-1379801
DOI: 10.1055/s-0034-1379801
Metal-Mediated Synthesis
Directed Regioselective 2,5- and 3,5-Dimagnesiations of Substituted Arenes
Further Information
Publication History
Publication Date:
19 January 2015 (online)
![](https://www.thieme-connect.de/media/synfacts/201502/i_p174_s1_10-1055_s-0034-1379801.gif)
Significance
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.
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Comment
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.
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![](https://www.thieme-connect.de/media/synfacts/201502/i_p174_s1_10-1055_s-0034-1379801.gif)