A novel and efficient arylation of malononitrile catalyzed by nickel(0) complexes

We report the first use of a nickel catalyst for the direct arylation of a β-difunctionalized compound, the malononitrile, from halogenated aromatic substrates. The catalytic system is quite simple: Ni(PPh 3) 3, generated in situ from NiBr 2(PPh 3) 2, PPh 3 and zinc. Good yields and excellent select...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 44; pp. 8457 - 8460
Main Authors Cristau, Henri Jean, Vogel, Rachel, Taillefer, Marc, Gadras, Alain
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.10.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BETA-DICARBONYL
ROUTE
ARYLMALONONITRILES
ORGANOBISMUTH REAGENTS
ACTIVE METHYLENE-COMPOUNDS
ARYL HALIDES
CHEMISTRY
AROMATIC-SUBSTITUTION
DERIVATIVES
SALTS
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Summary:We report the first use of a nickel catalyst for the direct arylation of a β-difunctionalized compound, the malononitrile, from halogenated aromatic substrates. The catalytic system is quite simple: Ni(PPh 3) 3, generated in situ from NiBr 2(PPh 3) 2, PPh 3 and zinc. Good yields and excellent selectivities have been obtained in α-arylmalononitriles from iodobenzene, but also from bromo- or chloro-aromatic substrates.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)01500-8