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

Matthias R Becker; Maximilian A Ganiek; Paul Knochel

doi:10.1039/c5sc02558c

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

Chem Sci. 2015 Nov 1;6(11):6649-6653. doi: 10.1039/c5sc02558c. Epub 2015 Aug 10.

Authors

Matthias R Becker¹, Maximilian A Ganiek¹, Paul Knochel¹

Affiliation

¹ Ludwig-Maximilians-Universität München , Department Chemie , Butenandtstrasse 5-13 (Haus F) , 81377 München , Germany . Email: paul.knochel@cup.uni-muenchen.de.

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.