Selective Lithiation, Magnesiation, and Zincation
of Unsymmetrical Azobenzenes Using Continuous Flow
Posted on 2017-03-15 - 16:34
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.
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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. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b00460