Chemistry: A European Journal 2015-03-27

Ru-catalysed C-H arylation of indoles and pyrroles with boronic acids: scope and mechanistic studies.

Carina Sollert, Karthik Devaraj, Andreas Orthaber, Paul J Gates, Lukasz T Pilarski

Index: Chemistry 21(14) , 5380-6, (2015)

Full Text: HTML

Abstract

The Ru-catalysed C2-H arylation of indoles and pyrroles by using boronic acids under oxidative conditions is reported. This reaction can be applied to tryptophan derivatives and tolerates a wide range of functional groups on both coupling partners, including bromides and iodides, which can be further derivatised selectively. New indole-based ruthenacyclic complexes are described and investigated as possible intermediates in the reaction. Mechanistic studies suggest the on-cycle intermediates do not possess a para-cymene ligand and that the on-cycle metalation occurs through an electrophilic attack by the Ru centre.© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.