Selective Lithiation, Magnesiation, and Zincation of Unsymmetrical Azobenzenes Using Continuous Flow

Marthe Ketels, David B. Konrad, Konstantin Karaghiosoff, Dirk Trauner, Paul Knochel

Research output: Contribution to journalArticle

Abstract

A mild and general set of metalation procedures for the functionalization of unsymmetrical azobenzenes using a commercially available continuous-flow setup is reported. The metalations proceed with TMPLi under convenient conditions (0 °C, 20 s), and various classes of electrophiles can be used. With sensitive substrates, an in situ trapping metalation in which TMPLi is added to a mixture of the azobenzene and ZnCl2 or MgCl2·LiCl was very effective for achieving high yields.

Original languageEnglish (US)
Pages (from-to)1666-1669
Number of pages4
JournalOrganic Letters
Volume19
Issue number7
DOIs
StatePublished - Apr 7 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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