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Synfacts 2025; 21(06): 606
DOI: 10.1055/a-2588-2885
Metals in Synthesis

Palladium-Catalyzed Direct C(sp2)–H Arylation of Benzene via Concerted Metalation–Deprotonation

Rezensent(en):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Finn H. Gattwinkel 
Lafrance M, Fagnou K *. University of Ottawa, Canada
Palladium-Catalyzed Benzene Arylation: Incorporation of Catalytic Pivalic Acid as a Proton Shuttle and a Key Element in Catalyst Design.

J. Am. Chem. Soc. 2006;
128: 16496-16497
DOI: 10.1021/ja067144j
CrossrefPubMedSuche in Google Scholar
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Keywords

concerted metalation–deprotonation (CMD) - C(sp2)−H activation - C(sp2)−H arylation - palladium catalysis - pivalic acid

Significance

While traditional cross-coupling reactions require the prefunctionalization of both coupling partners, Fagnou and Lafrance introduced a palladium(0)-catalyzed protocol for the direct C(sp2)–H arylation of unactivated benzene with aryl bromides. This approach does not require preformation of organometallic reagents.


 

Comment

Key to the success is the addition of pivalic acid as a co-catalyst. The pivalate acts as a cooperating ligand at the palladium and facilitates the C–H activation of benzene via a concerted metalation–deprotonation (CMD) process (see transition state in the catalytic cycle).


 

 

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Artikel online veröffentlicht:
22. Mai 2025

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