Lateral lithiation of N,N′-diaryl ureas

Jonathan Clayden*, Jérémy Dufour

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

29 Citations (Scopus)

Abstract

Aromatic ureas bearing N-(2-alkylaryl) groups may be laterally lithiated by treatment with sec-butyllithium. Quenching with a range of electrophiles yields functionalised aryl ureas in excellent yield. Lateral lithiation is favoured when the urea nitrogen adjacent to the aromatic ring in question is alkylated, and when competitive lithiations of such a ring are possible, lateral lithiation is more favourable than the alternative ortholithiation.

Original languageEnglish
Pages (from-to)6945-6946
Number of pages2
JournalTetrahedron Letters
Volume47
Issue number39
Early online date17 Aug 2006
DOIs
Publication statusPublished - 25 Sep 2006

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