Issue 47, 2021

Synthesis of 5,7-diarylindoles via Suzuki–Miyaura coupling in water

Abstract

The synthesis of novel 5,7-diaryl and diheteroaryl indoles has been explored via efficient double Suzuki–Miyaura coupling. The method notably employs a low catalyst loading of Pd(PPh3)4 (1.5 mol%/coupling) and water as the reaction solvent to obtain 5,7-diarylated indoles without using N-protecting groups in up to 91% yield. The approach is also suitable for N-protected and 3-substituted indoles and constitutes an important green and convenient arylation strategy for the benzenoid ring of indoles. The synthesized diarylindoles are fluorescent.

Graphical abstract: Synthesis of 5,7-diarylindoles via Suzuki–Miyaura coupling in water

Supplementary files

Article information

Article type
Paper
Submitted
20 Oct 2021
Accepted
16 Nov 2021
First published
16 Nov 2021
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2021,19, 10343-10347

Synthesis of 5,7-diarylindoles via Suzuki–Miyaura coupling in water

V. Elumalai and J. H. Hansen, Org. Biomol. Chem., 2021, 19, 10343 DOI: 10.1039/D1OB02058G

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