C-2 Selective Arylation of Indoles with Heterogeneous Nanopalladium and Diaryliodonium Salts
2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 42, 13531-13535 p.Article in journal (Refereed) Published
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 NH 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.
Place, publisher, year, edition, pages
Weinheim, 2014. Vol. 20, no 42, 13531-13535 p.
arylation, hypervalent iodine, indoles, nanopalladium, palladium catalysis
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-107700DOI: 10.1002/chem.201404017ISI: 000342797500013OAI: oai:DiVA.org:su-107700DiVA: diva2:749595
FunderBerzelii Centre EXSELENTEU, European Research Council, ERC AdG 247014Swedish Research Council, 621- 2011-3608Swedish Research Council, 621-2013-4653