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Practical and economic lithiations of functionalized arenes and heteroarenes using Cy2NLi in the presence of Mg, Zn or La halides in a continuous flow.


ABSTRACT: The economic amide base lithium dicyclohexylamide (Cy2NLi) allows fast and convenient (40 s, 0 °C) in situ trapping flow metalations of a broad range of functionalized arenes, heteroarenes and acrylate derivatives in the presence of various metal salts (ZnCl2·2LiCl, MgCl2, LaCl3·2LiCl). The resulting Zn-, Mg- or La-organometallic intermediates are trapped with various electrophiles in high yields. These flow metalations are easily scaled-up without further optimization.

SUBMITTER: Becker MR 

PROVIDER: S-EPMC5802273 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Practical and economic lithiations of functionalized arenes and heteroarenes using Cy<sub>2</sub>NLi in the presence of Mg, Zn or La halides in a continuous flow.

Becker Matthias R MR   Ganiek Maximilian A MA   Knochel Paul P  

Chemical science 20150810 11


The economic amide base lithium dicyclohexylamide (Cy<sub>2</sub>NLi) allows fast and convenient (40 s, 0 °C) <i>in situ</i> trapping flow metalations of a broad range of functionalized arenes, heteroarenes and acrylate derivatives in the presence of various metal salts (ZnCl<sub>2</sub>·2LiCl, MgCl<sub>2</sub>, LaCl<sub>3</sub>·2LiCl). The resulting Zn-, Mg- or La-organometallic intermediates are trapped with various electrophiles in high yields. These flow metalations are easily scaled-up with  ...[more]

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