Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones

Stabilized arylzinc iodides, synthesized by direct insertion of zinc into the corresponding halides, were used as nucleophiles into an acylative Negishi coupling reaction to synthesize chalcones. The reaction conditions were optimized to afford optimal results on a model reaction and then applied to...

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Bibliographic Details
Published in:Organics (Basel) 2022-06, Vol.3 (2), p.87-94
Main Authors: Pierigé, Michele, Iuliano, Anna, Angelici, Gaetano, Casotti, Gianluca
Format: Article
Language:English
Subjects:
acylative cross-coupling
arylzinc halides
chalcones
Chloride
cross-coupling
Flavonoids
Ligands
Negishi coupling
NMR
Nuclear magnetic resonance
organozinc halides
Palladium
Protocol
Reagents
Solvents
Zinc
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Summary:Stabilized arylzinc iodides, synthesized by direct insertion of zinc into the corresponding halides, were used as nucleophiles into an acylative Negishi coupling reaction to synthesize chalcones. The reaction conditions were optimized to afford optimal results on a model reaction and then applied to synthesize nine compounds. Esters, chlorides, electron-rich, electron-poor and sterically hindered substrates are well tolerated and even heteroaryl derivatives can be synthesized.
ISSN:2673-401X
2673-401X
DOI:10.3390/org3020006