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Synfacts 2015; 11(2): 0183
DOI: 10.1055/s-0034-1379801
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Directed Regioselective 2,5- and 3,5-Dimagnesiations of Substituted Arenes

Contributor(s):
Paul Knochel
,
Thomas Klatt
Martínez-Martínez AJ, Kennedy AR, Mulvey RE, * O’Hara CT. * University of Strathclyde, Glasgow, UK
Directed ortho-meta′- and meta-meta′-Dimetalations: A Template Base Approach to Deprotonation.

Science 2014;
346: 834-837
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Further Information

Publication History

Publication Date:
19 January 2015 (online)

 
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Key words

metalation - arenes - magnesium

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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