Issue 2, 2024

Gold catalysed regio- and chemoselective azo coupling of 1,2- and 1,4-diazoquinones with 1H-indoles

Abstract

A synthetic method to prepare (E)-3-arylazoindoles efficiently that relies on the gold(I)-catalysed azo coupling of 1,2- and 1,4-diazoquinones with 1H-indoles under mild reaction conditions that did not require the exclusion of air or moisture is described. The suggested azo coupling mechanistic pathway delineates the first instance of a α-diazocarbonyl compound acting as a N-centred electrophile instead of undergoing decomposition of the dinitrogen functional group. Experimental studies based on a (1H-indol-3-yl)gold species that is proposed to be preferentially generated from the direct reaction of the group 11 metal complex and N-heterocycle over α-diazocarbonyl compound decomposition provides insight into this observed product regio- and chemoselectivity. The utility of the synthetic method was exemplified by the efficient preparation of one example at the 2 mmol scale at a catalyst loading of 1 mol %, assembly of two known (E)-diazene-based molecular photoswitches and late-stage functionalisation of two biologically relevant molecules.

Graphical abstract: Gold catalysed regio- and chemoselective azo coupling of 1,2- and 1,4-diazoquinones with 1H-indoles

Supplementary files

Article information

Article type
Research Article
Submitted
12 Okt. 2023
Accepted
08 Nov. 2023
First published
17 Nov. 2023

Org. Chem. Front., 2024,11, 290-298

Gold catalysed regio- and chemoselective azo coupling of 1,2- and 1,4-diazoquinones with 1H-indoles

J. Jin, A. F. León Rojas, Y. Zhao, S. Helen Kyne, B. Xia, B. Zhong and P. W. H. Chan, Org. Chem. Front., 2024, 11, 290 DOI: 10.1039/D3QO01676E

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