Beyond Aresta’s Complex: Ni- and Pd-Catalyzed Organozinc Coupling with CO2

Organozinc reagents are widely used in organic synthesis due primarily to their high functional group compatibility. However, under mild conditions, these organometallic reagents do not react directly with CO2, the ideal C1 source for organic synthesis. Herein, we report that both Ni and Pd complexe...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 130; no. 25; pp. 7826 - 7827
Main Authors Yeung, Charles S, Dong, Vy M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.06.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
SYSTEM
ACTIVATION
CARBOXYLATION
NICKEL
CARBON-DIOXIDE
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Summary:Organozinc reagents are widely used in organic synthesis due primarily to their high functional group compatibility. However, under mild conditions, these organometallic reagents do not react directly with CO2, the ideal C1 source for organic synthesis. Herein, we report that both Ni and Pd complexes can catalyze the addition of organozinc reagents to CO2 under mild conditions (1 atm CO2, 0 °C). This transformation represents an important extension of the Negishi cross-coupling and is believed to occur via a novel mechanism involving Aresta’s complex and/or its corresponding Pd analogue.
Bibliography:istex:CD1C5A3B3E3F19891264D3E9A3ED890156A44D96
General procedures for carboxylations, organozinc synthesis, catalyst preparation, spectroscopic data. This material is available free of charge via the Internet at http://pubs.acs.org.
ark:/67375/TPS-T47P6H1S-Q
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja803435w