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Atroposelective interrupted CuAAC reaction using cyclic diaryliodoniums.

Yuanyuan Li¹, Shan Yang¹, Longhui Duan¹

¹Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, PR China.

Nature Communications

|January 24, 2026

Summary

This summary is machine-generated.

This study introduces an asymmetric interrupted copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. It efficiently synthesizes unique atropisomeric biaryl triazoles using a novel three-component coupling strategy.

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Area of Science:

Organic Chemistry
Catalysis
Asymmetric Synthesis

Background:

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a versatile method for fragment coupling.
Interrupted CuAAC reactions broaden synthetic scope by utilizing copper triazolide intermediates.
Asymmetric versions of interrupted CuAAC reactions were previously undeveloped.

Purpose of the Study:

To develop an efficient and mild asymmetric interrupted CuAAC reaction.
To enable atroposelective synthesis of biaryl triazoles.
To investigate the reaction mechanism and kinetics.

Main Methods:

Intercepting a copper triazolide intermediate with a cyclic diaryliodonium reagent.
Employing a three-component coupling of cyclic diaryliodonium, alkyne, and azide.
Utilizing in situ calorimetry for reaction progress kinetic analysis.

Main Results:

Successful development of an asymmetric interrupted CuAAC reaction.
Synthesis of diverse atropisomeric biaryl triazoles.
Identification of a secondary kinetic isotope effect and substrate reaction orders.

Conclusions:

The presented method provides an efficient route to complex atropisomeric biaryl triazoles.
The reaction proceeds via copper-mediated cyclometallation and oxidative addition.
This work expands the utility of interrupted CuAAC reactions in asymmetric synthesis.