Lithium Dicyclohexylamide - Practical and Economic Lithiations of Functionalised Arenes and Heteroarenes in Flow

The economic amide base lithium dicyclohexylamide (Cy₂NLi) allows fast and convenient (40s, 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.

 Lithium Dicyclohexylamide - Practical and Economic Lithiations of Functionalised Arenes and Heteroarenes in Flow

M. R. Becker, M. A. Ganiek amd P. Knochel, Chem. Sci., 2015, 6, 6649

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,^a   Maximilian A. Ganiek^a and   Paul Knochel*^a  

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Corresponding authors

^a

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

Chem. Sci., 2015,6, 6649-6653

DOI: 10.1039/C5SC02558C
 http://pubs.rsc.org/en/content/articlelanding/2015/sc/c5sc02558c#!divAbstract


 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.


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