Synlett 2017; 28(08): 907-912
DOI: 10.1055/s-0036-1588719
letter
© Georg Thieme Verlag Stuttgart · New York

Visible-Light Photocatalytic Double C–H Functionalization of Indoles: A Synergistic Experimental and Computational Study

Uranbaatar Erdenebilega, Taye B. Demissieb, Jørn H. Hansen*a
  • aDepartment of Chemistry, UiT The Arctic University of Norway, Hansine Hansens veg 54, 9037 Tromsø, Norway   Email: jorn.h.hansen@uit.no
  • bCentre for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, UiT The Arctic University of Norway, 9037 Tromsø, Norway
Further Information

Publication History

Received: 14 November 2016

Accepted after revision: 26 January 2017

Publication Date:
21 February 2017 (eFirst)

Abstract

Herein is disclosed a novel visible-light photocatalytic double C–H functionalization of indoles. The reaction affords 2,3-difunctionalized indoles in up to 84% yield, but the reaction rate depends strongly on electronic substituent effects. Mechanistic DFT studies and control experiments suggest that the secondary functionalization occurs through an independent photocatalytic oxidation of bromide ions formed during the reaction to generate molecular bromine capable of electrophilic C-3 bromination.

Supporting Information