Ru-catalysed C-H Arylation of Indoles and Pyrroles with Boronic Acids: Scope and Mechanistic Studies

Overview

Journal Chemistry

Specialty Chemistry

Date 2015 Feb 18

PMID 25689052

Citations 11

Authors

Carina Sollert

Karthik Devaraj

Andreas Orthaber

Paul J Gates

Lukasz T Pilarski

Affiliations

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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.

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