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Visible‐Light‐Driven Chemoselective Hydrogenation of Nitroarenes to Anilines in Water through Graphitic Carbon Nitride Metal‐Free Photocatalysis
Author(s) -
Xiao Gang,
Li Peifeng,
Zhao Yilin,
Xu Shengnan,
Su Haijia
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800515
Subject(s) - photocatalysis , aniline , graphitic carbon nitride , catalysis , carbon nitride , visible spectrum , yield (engineering) , carbon fibers , chemistry , photochemistry , materials science , organic chemistry , composite number , optoelectronics , metallurgy , composite material
Green and efficient procedures are essential for the chemoselective hydrogenation of functionalized nitroarenes to form industrially important anilines. Herein, it is shown that visible‐light‐driven, chemoselective hydrogenation of functionalized nitroarenes with groups sensitive to forming anilines can be achieved in good to excellent yields (82–100 %) in water under relatively mild conditions and catalyzed by low‐cost and recyclable graphitic carbon nitride. The process is also applicable to gram‐scale reaction, with a yield of aniline of 86 %. A study of the mechanism reveals that visible‐light‐induced electrons are responsible for the hydrogenation reactions, and thermal energy can also promote the photocatalytic activity. A study of the kinetics shows that this reaction possibly occurs through one‐step hydrogenation or stepwise condensation routes. A wide range of applications can be expected for this green, efficient, and highly selective photocatalysis system in reduction reactions for the synthesis of fine chemicals.