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