Abstract
Herein, an easily accessible and efficient green method for the reduction of nitroarene compounds was developed using metal oxide catalysts. Heterogeneous metal oxides with or without Pd were prepared by a simple and scalable co-precipitation method and used for the reduction of nitroarenes. A fluorescence-based high-throughput screening (HTS) method was also developed for the rapid analysis of the reaction conditions. The catalytic activity of the metal oxides and reaction conditions were rapidly screened by the fluorescence-based HTS method, and Pd/CuO showed the highest catalytic activity under mild reaction conditions. After identifying the optimal reaction conditions, various nitroarenes were reduced to the corresponding aniline derivatives by Pd/CuO (0.005 mol% of Pd) under these conditions. Furthermore, the Pd/CuO catalyst was used for the one-pot Suzuki–Miyaura cross-coupling/reduction reaction. A gram-scale reaction (20 mmol) was successfully performed using the present method, and Pd/CuO showed high reusability without a loss of catalytic activity for five cycles.
Highlights
The synthesis of highly functionalized aniline derivatives is an important chemical reaction, because these derivatives are key intermediates in the production of valuable chemicals including pharmaceuticals, agrochemicals, dyes, and polymers [1]
The present fluorescence-based high-throughput screening (HTS) method was developed to evaluate the catalytic activity of metal oxides for the reduction of nitroarenes
The transformation of a nitro group to the amine has been widely used in the development of chemosensors for targets or enzyme assay because corresponding amine has been widely used in the development of chemosensors for targets or the reaction induces a dramatic change in the chemosensor signal [51,52,53]
Summary
The synthesis of highly functionalized aniline derivatives is an important chemical reaction, because these derivatives are key intermediates in the production of valuable chemicals including pharmaceuticals, agrochemicals, dyes, and polymers [1]. Zn, and Ni [2,3,4,5] These methods have some drawbacks, such as the use of toxic organic solvents, expensive hydrides, flammable hydrogen gas, high-pressure equipment, and a large amount of expensive metal catalysts. The latter could result in high levels of residual metals in the product, which is a serious problem in pharmaceutical chemistry [6]. Some methods require harsh reaction conditions, such as acidic pHs and high temperatures These conditions hinder the application of the method to nitro compounds containing sensitive functional groups. Several methods using Pd nanoparticles (NPs)-based catalysts, such as Pd NPs in nanomicelle [7,8]
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