Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation

Jonathan Clayden*, Hazel Turner, Mark Pickworth, Thomas Adler

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

35 Citations (Scopus)

Abstract

(Chemical Equation Presented) Unsymmetrical N,N′-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.

Original languageEnglish
Pages (from-to)3147-3150
Number of pages4
JournalOrganic Letters
Volume7
Issue number15
Early online date29 Jun 2005
DOIs
Publication statusPublished - 21 Jul 2005

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