Issue 5, 2023

Heterocyclic Suzuki–Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity

Abstract

Pd-catalyzed Suzuki–Miyaura cross-coupling is one of the most straightforward and versatile methods for the construction of functionalized arenes and heteroarenes but site-selective cross-coupling of polyhalogenated (hetero)arenes containing identical halogen substituents remains a challenging problem. Herein, we report a new candidate for heterocyclic Suzuki–Miyaura coupling reaction. This candidate has been applied in organometallic systems by combining classical aryl boronic acid reagents with non-classical heteroarenes. Experimental and computational studies of the mechanism of the reactions were performed, with an emphasis on the identity of the reactive species in the oxidative addition step and the nature of the precise site selectivity. The influence of both the aromaticity of the metalla-aromatic substrates and the steric and electronic properties of the halogenated sites are studied in detail.

Graphical abstract: Heterocyclic Suzuki–Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Sep 2022
Accepted
29 Dec 2022
First published
02 Jan 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 1227-1233

Heterocyclic Suzuki–Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity

Z. Lin, Y. Cai, Y. Zhang, H. Zhang and H. Xia, Chem. Sci., 2023, 14, 1227 DOI: 10.1039/D2SC05455H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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