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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Published inAngewandte Chemie (International ed.) Vol. 43; no. 8; pp. 1017 - 1021
Main Authors Kneisel, Florian F., Dochnahl, Maximilian, Knochel, Paul
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 13.02.2004
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
copper
cross-coupling
iodine-zinc exchange
nucleophilic catalysis
palladium
Physical Sciences
Science & Technology
HALIDES
REAGENTS
ATE COMPLEXES
ORGANOMETALLICS
ARYLMAGNESIUM
iodine-zinc exchange
PRIMARY ALKYL IODIDES
MAGNESIUM
nucleophilic catalysis
cross-coupling
copper
palladium
ARYL
LITHIUM
DERIVATIVES
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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.
Bibliography:We thank the Deutsche Forschungsgemeinschaft for a fellowship to F.F.K. (KN 347/6-1) and the Fonds der Chemischen Industrie for generous financial support. We thank BASF AG (Ludwigshafen) and Chemetall GmbH (Frankfurt) for generous gifts of chemicals and Florence Darbour for preliminary experiments.
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ArticleID:ANIE200353316
We thank the Deutsche Forschungsgemeinschaft for a fellowship to F.F.K. (KN 347/6‐1) and the Fonds der Chemischen Industrie for generous financial support. We thank BASF AG (Ludwigshafen) and Chemetall GmbH (Frankfurt) for generous gifts of chemicals and Florence Darbour for preliminary experiments.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353316