Synthesis of Allylarenes via Catalytic Decarboxylation of Allyl Benzoates

Synthesis of Allylarenes via Catalytic Decarboxylation of Allyl Benzoates

A catalyst system consisting of the palladium(0) complex Pd2(dba)3 and tri(p‐tolyl)phosphine was found to efficiently promote the decarboxylation of allyl benzoates with formation of allylarenes. This catalytic CO activation followed by extrusion of carbon dioxide and CC bond formation represents...

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Veröffentlicht in:Advanced synthesis & catalysis 2014-11, Vol.356 (16), p.3302-3306
Hauptverfasser: Pfister, Kai F., Grünberg, Matthias F., Gooßen, Lukas J.
Format: Artikel
Sprache:eng
Schlagworte:
allylation
Benzoates
Carbon dioxide
Catalysis
Catalysts
Decarboxylation
Esters
homogeneous catalysis
nickel
palladium
Synthesis
Transformations
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Zusammenfassung:A catalyst system consisting of the palladium(0) complex Pd2(dba)3 and tri(p‐tolyl)phosphine was found to efficiently promote the decarboxylation of allyl benzoates with formation of allylarenes. This catalytic CO activation followed by extrusion of carbon dioxide and CC bond formation represents a sustainable alternative to traditional waste‐intensive cross‐couplings. The scope of the transformation includes allyl and cinnamyl esters of various ortho‐substituted benzoic acids. For particularly activated substrates, the palladium catalyst can optionally be replaced by an inexpensive nickel complex.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400624