Issue 1, 2024

A simple method for N-arylation of secondary amides/amines through a NaH-initiated aryne generation strategy

Abstract

A very simple and practical method has been uncovered for N-arylation of many sets of secondary amides/amines. The reaction could be easily conducted in a vial without the use of strictly anhydrous reagents and/or an inert atmosphere. This transition metal-free coupling reaction was based on the use of our previously reported novel aryne generation system: a combination of o-diiodoarene and sodium hydride. In our protocol, sodium hydride acts as an iodophile by forming a neighboring-group-assisted transition state with o-diiodoarene, which greatly enhances the metal–halogen exchange process. o-Diiodoarene has two roles in the reaction: (i) as an aryne precursor to produce an aryne at near room temperature and (ii) as an electrophilic iodine donor to support the generation of the final o-iodoaryl product. The generality of the method is demonstrated by 99 examples containing almost all kinds of amides and amines.

Graphical abstract: A simple method for N-arylation of secondary amides/amines through a NaH-initiated aryne generation strategy

Supplementary files

Article information

Article type
Research Article
Submitted
19 Jul 2023
Accepted
02 Oct 2023
First published
03 Oct 2023

Org. Chem. Front., 2024,11, 12-20

A simple method for N-arylation of secondary amides/amines through a NaH-initiated aryne generation strategy

Y. Jiang, W. Zhu, J. Huang, F. Luo, X. Chen, C. Fang, X. Chen, S. Liu, Y. Hu and S. Zhang, Org. Chem. Front., 2024, 11, 12 DOI: 10.1039/D3QO01109G

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