Issue 4, 2022

RhIII-Catalyzed heteroarylation of N-2,6-difluorophenyl arylamides with heteroaryl boronate esters

Abstract

Herein, an efficient strategy to achieve aryl-heteroaryl formation via RhIII-catalyzed ortho-C(sp2)–H heteroarylation of (hetero)arenes with heterocyclic boronates using a readily removable N-2,6-difluorophenyl arylamide directing group has been disclosed. A variety of heteroaromatic boronates as the coupling partners were shown to be able to participate in this protocol, providing the desired heteroarylated products with high reactivity and good tolerance of functional groups. The achievement of this C(sp2)–H heteroarylation could potentially offer a route to synthesize heterocyclic drug molecules in medicinal chemistry.

Graphical abstract: RhIII-Catalyzed heteroarylation of N-2,6-difluorophenyl arylamides with heteroaryl boronate esters

Supplementary files

Article information

Article type
Research Article
Submitted
14 Dec 2021
Accepted
28 Dec 2021
First published
29 Dec 2021

Org. Chem. Front., 2022,9, 1077-1084

RhIII-Catalyzed heteroarylation of N-2,6-difluorophenyl arylamides with heteroaryl boronate esters

J. Wu, Q. Yao, W. Duan, D. Li, X. Huang, J. Dou and H. Wang, Org. Chem. Front., 2022, 9, 1077 DOI: 10.1039/D1QO01868J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements