New preparation of TMPZnCl·LiCl by Zn insertion into TMPCl. Application to the functionalization of dibromodiazines.

Andreas Unsinn, Mark J Ford, Paul Knochel

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany.

Organic letters 2013 Mar 1

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A practical zinc insertion starting from cheap commercial zinc powder and TMPCl (1-chloro-2,2,6,6-tetramethylpiperidine) allows a fast and efficient synthesis of the zinc base TMPZnCl·LiCl under mild conditions in high yields. This base is kinetically highly active and was used for the regio- and chemoselective functionalization of dibromodiazines (pyridazines and pyrazines).

Citation

Andreas Unsinn, Mark J Ford, Paul Knochel. New preparation of TMPZnCl·LiCl by Zn insertion into TMPCl. Application to the functionalization of dibromodiazines. Organic letters. 2013 Mar 1;15(5):1128-31