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

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azobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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Selective Lithiation, Magnesiation, and Zincation of Unsymmetrical Azobenzenes Using Continuous Flow. / Ketels, Marthe; Konrad, David B.; Karaghiosoff, Konstantin; Trauner, Dirk; Knochel, Paul.

In: Organic Letters, Vol. 19, No. 7, 07.04.2017, p. 1666-1669.

Research output: Contribution to journalArticle

Ketels, M, Konrad, DB, Karaghiosoff, K, Trauner, D & Knochel, P 2017, 'Selective Lithiation, Magnesiation, and Zincation of Unsymmetrical Azobenzenes Using Continuous Flow', Organic Letters, vol. 19, no. 7, pp. 1666-1669. https://doi.org/10.1021/acs.orglett.7b00460
Ketels, Marthe ; Konrad, David B. ; Karaghiosoff, Konstantin ; Trauner, Dirk ; Knochel, Paul. / Selective Lithiation, Magnesiation, and Zincation of Unsymmetrical Azobenzenes Using Continuous Flow. In: Organic Letters. 2017 ; Vol. 19, No. 7. pp. 1666-1669.
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