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

Ketels, Marthe; Konrad, David B.; Karaghiosoff, Konstantin; Trauner, Dirk and Knochel, Paul (2017): Selective Lithiation, Magnesiation, and Zincation of Unsymmetrical Azobenzenes Using Continuous Flow. In: Organic Letters, Vol. 19, No. 7: pp. 1666-1669

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-omicron, 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 center dot LiCl was very effective for achieving high yields.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English