Palladium catalyzed synthesis of 4-substituted-2-phenylimidazoles from N-propargyl-benzamidine

Preliminary results of an original approach to 4-substituted-2-phenylimidazoles starting from readily available N-propargyl-benzamidine and aryl halides are reported. Best yields were obtained using aryl halides bearing an electron-withdrawing group. Plausible mechanisms are also discussed.

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 48; pp. 8491 - 8495
Main Authors Abbiati, Giorgio, Arcadi, Antonio, Canevari, Valentina, Rossi, Elisabetta
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.11.2007
Elsevier
Subjects
Alkynes
Amidine
Aminopalladation
Chemistry
Chemistry, Organic
Domino reaction
Homogeneous catalysis
Imidazole
Palladium
Physical Sciences
Science & Technology
Amidine
Imidazole
Homogeneous catalysis
Palladium
Aminopalladation
Alkynes
Domino reaction
ACETYLENES
imidazole
alkynes
aminopalladation
amidine
IMIDAZOLES
REDUCTIVE ELIMINATION
INDOLES
homogeneous catalysis
AMINES
CHLORIDES
palladium
ARYL IODIDES
DERIVATIVES
CYCLIZATION
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Summary:Preliminary results of an original approach to 4-substituted-2-phenylimidazoles starting from readily available N-propargyl-benzamidine and aryl halides are reported. Best yields were obtained using aryl halides bearing an electron-withdrawing group. Plausible mechanisms are also discussed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.09.153