Aerobic Catalytic Cross‐Dehydrogenative Coupling of Furans with Indoles Provides Access to Fluorophores with Large Stokes Shift

Author:

Mhaske Krishna1ORCID,Gangai Shon1,Fernandes Rushil1,Kamble Angulimal1,Chowdhury Arkaprava2ORCID,Narayan Rishikesh13ORCID

Affiliation:

1. School of Chemical and Materials Sciences Indian Institute of Technology Goa, Farmagudi Goa 403401 India

2. Department of Chemistry Indian Institute of Technology Bombay Mumbai 400076 Maharashtra India

3. School of Interdisciplinary Life Sciences Indian Institute of Technology Goa, Farmagudi Goa 403401 India

Abstract

AbstractSustainability in chemical processes is a crucial aspect in contemporary chemistry with sustainable catalysis as a vital parameter of the same. There has been a renewed focus on utilizing earth‐abundant metal catalysts to expand the repertoire of organic reactions. Furan is a versatile heterocycle of natural origin used for multiple applications. However, it has scarcely been used in cross‐dehydrogenative coupling. In this work, we have explored the cross‐dehydrogentive coupling of furans with indoles using commonly available, inexpensive FeCl3 ⋅ 6H2O (<0.25 $/g) as catalyst in the presence of so called ‘ultimate oxidant’ – oxygen, without the need for any external ligand or additive. The reactions were found to be scalable and to work even under partially aqueous conditions. This makes the reaction highly economical, practical, operationally simple and sustainable. The methodology provides direct access to π‐conjugated short oligomers consisting of furan, thiophene and indole. These compounds were found to show interesting fluorescence properties with remarkably large Stokes shift (up to 205 nm). Mechanistic investigations reveal that the reaction proceeds through chemoselective oxidation of indole by the metal catalyst followed by nucleophilic trapping by furan.

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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