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Synfacts 2013; 9(9): 0991
DOI: 10.1055/s-0033-1339561
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Fe-, Co- and Cu-Catalyzed Coupling Reactions Using N2O

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Kiefer G, Jeanbourquin L, Severin K * Ecole Polytechnique Fédérale de Lausanne, Switzerland
Oxidative Coupling Reactions of Grignard Reagents with Nitrous Oxide.

Angew. Chem. Int. Ed. 2013;
52: 6302-6305
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Further Information

Publication History

Publication Date:
19 August 2013 (online)

 
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Key words

nitrous oxide - iron - cobalt

Significance

For the first time, N2O (‘laughing gas’) is reported to undergo oxidative homo-coupling reactions of Grignard reagents in the presence of metal catalysts under mild reaction conditions. Whereas less than 1 mol% of Fe(acac)3 and CoCl2 showed to be superior in the homo-coupling reactions of arylmagnesium reagents, also alkyl Grignard reagents undergo oxidative homo-coupling reactions in the presence of Li2CuCl4.


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Comment

The authors applied this new protocol also to oxidative cross-coupling reactions between sp2- and sp3-hybridized Grignard reagents. Therefore, PhMgCl and various primary and secondary alkyl Grignard reagents furnish the desired aryl–alkyl cross-coupling products in 59–83% yield.


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