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Synfacts 2006(8): 0860-0860  
DOI: 10.1055/s-2006-941991
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Indoles Using Heterogeneous Pd Catalysts

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
L. Djakovitch*, V. Dufaud, R. Zaidi
Institut de Recherches sur la Catalyse, Villeurbanne and Ecole Normale Supérieure de Lyon, France
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Publikationsdatum:
21. Juli 2006 (online)

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Significance

A one-pot synthesis of indoles was successfully achieved by use of palladium-exchanged microporous NaY zeolite {[Pd(NH3)4]2+/NaY} and mesoporous SBA-15 type silica-supported palladium catalyst ([Pd]/SBA-15). The reaction of 2-iodoanilines with phenyl- and alkyl-substituted terminal alkynes took place in the presence of [Pd(NH3)4]2+/NaY or [Pd]/SBA-15 to give 2-substituted indoles in 74-95% yield (eq. 1). The arylation of 2-phenylindole with aryl bromides took place at the C3-position of the indole ring to give 3-arylindoles, whereas the arylation with aryl iodide proceeded at the nitrogen atom to give N-arylindoles (eqs 2 and 3).