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Photo-Induced Intermolecular N-N Cross-Coupling via Nitrene Transfer Reaction.

Subrata Das¹, Hillol Khatua¹, Demi D Snabilié²

¹Department of Chemistry, Indian Institute of Science Education and Research (IISER) Pune, Dr. Homi Bhabha Road, Pashan, Pune, Maharashtra 411008, India.

Journal of the American Chemical Society

|December 8, 2025

Summary

This summary is machine-generated.

A new light-induced N-N cross-coupling reaction uses pyrido-oxazolones as nitrene precursors. This metal-free method efficiently synthesizes hydrazides at room temperature, useful for drug development.

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Published on: January 21, 2020

Area of Science:

Organic Chemistry
Photochemistry
Medicinal Chemistry

Background:

Metal-free cross-coupling reactions are crucial for synthesizing complex organic molecules.
Nitrene precursors are valuable intermediates in organic synthesis.
Late-stage functionalization of bioactive molecules remains a challenge.

Purpose of the Study:

To develop a novel, metal-free intermolecular N-N cross-coupling reaction.
To utilize pyrido-oxazolones as efficient nitrene precursors under photoinduced conditions.
To establish a streamlined protocol for synthesizing diverse hydrazides.

Main Methods:

Photoactivation of pyrido-oxazolones to generate nitrenes.
Intermolecular N-N cross-coupling with N-alkyl or N-aryl anilines.
Mechanistic studies including theoretical calculations.

Main Results:

Successful metal-free N-N cross-coupling reaction under light.
Synthesis of a diverse range of hydrazides at room temperature.
Demonstration of operational simplicity and late-stage functionalization capability.

Conclusions:

Pyrido-oxazolones are effective nitrene precursors for photoinduced N-N cross-coupling.
The developed method offers a streamlined synthetic route to hydrazides.
This reaction holds significant potential for medicinal chemistry and drug development.