C‐2 Selective Arylation of Indoles with Heterogeneous Nanopalladium and Diaryliodonium Salts |
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| Authors: | Joel Malmgren Anuja Nagendiran Dr Cheuk‐Wai Tai Prof Jan‐E Bäckvall Prof Berit Olofsson |
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| Affiliation: | 1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46)?8‐154908;2. Department of Materials and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden) |
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| Abstract: | A simple and efficient method to prepare synthetically useful 2‐arylindoles is presented, using a heterogeneous Pd catalyst and diaryliodonium salts in water under mild conditions. A remarkably low leaching of metal catalyst was observed under the applied conditions. The developed protocol is highly C‐2 selective and tolerates structural variations both in the indole and in the diaryliodonium salt. Arylations of both N?H indoles and N‐protected indoles with ortho‐substituted, electron‐rich, electron‐deficient, or halogenated diaryliodonium salts were achieved to give the desired products in high to excellent isolated yields within 6 to 15 h at room temperature or 40 °C. |
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| Keywords: | arylation hypervalent iodine indoles nanopalladium palladium catalysis |
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