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Controlling chemoselectivity in the lithiation of substituted aromatic tertiary amides

Solvent effects control the regioselectivity with which tert-butyllithium deprotonates 2-ethyl-N,N-diisopropyl-1-benzamide. From THF an ortho-lithiated dimer is isolated but from N,N,N?,N?, N?pentamethyldiethylenetriamine (pmdeta) a laterally lithiated monomer is obtained (see scheme). Density functional theory (DFT) calculations point to the importance of Lewis base solvation and aggregation state in determining the chemoselectivity.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI