One-pot selective synthesis of azoxy compounds and imines via the photoredox reaction of nitroaromatic compounds and amines in water.

Abstract:

:A facile one-pot two-stage photochemical synthesis of aromatic azoxy compounds and imines has been developed by coupling the selective reduction of nitroaromatic compounds with the selective oxidation of amines in an aqueous solution. In the first stage (light illumination, Ar atmosphere), the light excited nitroaromatic molecule abstract H from amine to form ArNO2H and amine radical, which then form nitrosoaromatic, hydroxylamine and imine compounds. Water acts as a green solvent for the dispersion of the reactants and facilitates the formation of nitrosoaromatic and hydroxylamine intermediate compounds. In the second stage (no light, air atmosphere), the condensation of nitrosoaromatic and hydroxylamine compounds yields aromatic azoxy product with the aid of molecular oxygen in air. This photochemical synthesis achieved both high conversion and high product selectivity (>99%) at room temperature.

journal_name

Sci Rep

journal_title

Scientific reports

authors

Tan H,Liu X,Su J,Wang Y,Gu X,Yang D,Waclawik ER,Zhu H,Zheng Z

doi

10.1038/s41598-018-38100-6

subject

Has Abstract

pub_date

2019-02-04 00:00:00

pages

1280

issue

1

issn

2045-2322

pii

10.1038/s41598-018-38100-6

journal_volume

9

pub_type

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