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Synfacts 2015; 11(1): 0101
DOI: 10.1055/s-0034-1379722
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Heterogeneous Palladium Catalyst for C2-Selective Arylation of Indoles

Rezensent(en):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Rikako Ishii
Malmgren J, Nagendiran A, Tai C.-W, Bäckvall JE, * Olofsson B. * Stockholm University, Sweden
C2-Selective Arylation of Indoles with Heterogeneous Nanopalladium and Diaryliodonium Salts.

Chem. Eur. J. 2014;
20: 13531-13535
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Publikationsverlauf

Publikationsdatum:
15. Dezember 2014 (online)

 
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Key words

arylation - diaryliodonium salts - indoles - palladium catalysis

Significance

Pd0-AmP-MCF constitutes of silica-based mesocellular foam (MCF) functionalized with aminopropylsilane (for the preparation, see: M. Shakeri et al. Chem. Eur. J. 2011, 17, 13269). Pd0-AmP-MCF (palladium particles ø: 2–3 nm) catalyzed the C2-selective arylation of indoles 1 and substituted diaryliodonium tetrafluoroborates 2 to give the corresponding indole derivatives in 65–99% yield (15 examples).


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Comment

The reactions of an electron-rich indole (3b), an N-methylated indole (3d), para-alkyl-substituted salts (3f,g), or an electron-deficient CF3-substituted salt (3j) afforded high yields, whereas an N-benzylated indole (3e) or a naphthyl salt (3i) resulted in lower yield. ICP-OES analysis showed 0.6 ppm of palladium leaching from the reaction mixture (3a).


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