New Preparation of TMPZnCl·LiCl by Zn Insertion into TMPCl. Application to the Functionalization of Dibromodiazines

New Preparation of TMPZnCl·LiCl by Zn Insertion into TMPCl. Application to the Functionalization of Dibromodiazines

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 ch...

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Veröffentlicht in:Organic letters 2013-03, Vol.15 (5), p.1128-1131
Hauptverfasser: Unsinn, Andreas, Ford, Mark J, Knochel, Paul
Format: Artikel
Sprache:eng
Schlagworte:
Combinatorial Chemistry Techniques
Hydrocarbons, Chlorinated - chemical synthesis
Hydrocarbons, Chlorinated - chemistry
Lithium - chemistry
Molecular Structure
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Piperidines - chemistry
Pyridazines - chemical synthesis
Pyridazines - chemistry
Stereoisomerism
Zinc - chemistry
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Zusammenfassung: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400248e