Controlling chemoselectivity in the lithiation of substituted aromatic tertiary amides

David R. Armstrong, Sally R. Boss*, Jonathan Clayden, Robert Haigh, Basel A. Kirmani, David J. Linton, Paul Schooler, Andrew E H Wheatley

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

24 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2135-2138
Number of pages4
JournalAngewandte Chemie - International Edition
Volume43
Issue number16
Early online date6 Apr 2004
DOIs
Publication statusPublished - 13 Apr 2004

Keywords

  • Density functional calculations
  • Directing groups
  • Lithiation
  • Reaction mechanisms
  • Solid-state structures

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