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Abstract
The regioselectivity of deprotonation reactions between arene substrates and basic metalating agents is usually governed by the electronic and/or coordinative characteristics of a directing group attached to the benzene ring. Generally, the reaction takes place in the ortho position, adjacent to the substituent. Here, we introduce a protocol by which the metalating agent, a disodium-monomagnesium alkyl-amide, forms a template that extends regioselectivity to more distant arene sites. Depending on the nature of the directing group, ortho-meta' or meta-meta' dimetalation is observed, in the latter case breaking the dogma of ortho metalation. This concept is elaborated through the characterization of both organometallic intermediates and electrophilically quenched products.
Original language | English |
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Pages (from-to) | 834-837 |
Number of pages | 4 |
Journal | Science |
Volume | 346 |
Issue number | 6211 |
DOIs | |
Publication status | Published - 14 Nov 2014 |
Keywords
- benzene
- organometallic compound
- reaction kinetics
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Projects
- 3 Finished
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Chiral Concepts in s-Block Metal Amide Chemistry
EPSRC (Engineering and Physical Sciences Research Council)
1/10/11 → 30/09/16
Project: Research Fellowship
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