Nucleophilic Catalysis of the Iodine-Zinc Exchange Reaction: Preparation of Highly Functionalized Diaryl Zinc Compounds

Sensitive functional groups are tolerated in an iodine–zinc exchange reaction catalyzed by Li(acac). Aryl and heteroaryl diorganozinc compounds with keto, aldehyde, or isothiocyanate substituents can be prepared by this method (see example in scheme; acac=acetylacetone, NMP=1‐methyl‐2‐pyrrolidinone)...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-02, Vol.43 (8), p.1017-1021
Main Authors: Kneisel, Florian F., Dochnahl, Maximilian, Knochel, Paul
Format: Article
Language:English
Subjects:
copper
cross-coupling
iodine-zinc exchange
nucleophilic catalysis
palladium
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Summary:Sensitive functional groups are tolerated in an iodine–zinc exchange reaction catalyzed by Li(acac). Aryl and heteroaryl diorganozinc compounds with keto, aldehyde, or isothiocyanate substituents can be prepared by this method (see example in scheme; acac=acetylacetone, NMP=1‐methyl‐2‐pyrrolidinone). Such zinc reagents serve as substrates for a wide variety of coupling reactions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353316