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. 2022 Sep 23;7(39):35170-35179.
doi: 10.1021/acsomega.2c04196. eCollection 2022 Oct 4.

Organocatalytic Reduction of Aromatic Nitro Compounds: The Use of Solid-Supported Phenyl(2-quinolyl)methanol

Donatella Giomi  1 , Jacopo Ceccarelli  2 , Antonella Salvini  1 , Marika Pinto  1 , Alberto Brandi  1
Affiliations

Organocatalytic Reduction of Aromatic Nitro Compounds: The Use of Solid-Supported Phenyl(2-quinolyl)methanol

Donatella Giomi et al. ACS Omega. .

Abstract

The reduction of aromatic nitro compounds has been performed employing a catalytic amount of Wang resin-supported phenyl(2-quinolyl)methanol (Wang-PQM) in the presence of an excess of NaBH4 to regenerate the reactive reducing species at the end of the process. The reduction products are easily isolated through a simple filtration/extraction protocol, and the catalyst can be efficiently recovered and recycled. The condensation route is generally preferred, and azo- and/or hydrazo-arenes can be easily prepared in high yields.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Haber Mechanism for Nitroarene Reduction
Figure 1
Figure 1
Retrosynthetic analyses to access solid-supported PQMs.
Scheme 2
Scheme 2. Synthesis of QTM (1) and QTK (2)
Scheme 3
Scheme 3. Synthesis of Merrifield-QTK (3)
Scheme 4
Scheme 4. Synthesis of (4-bromomethylphenyl)(2-quinolyl)methanone (4)
Scheme 5
Scheme 5. Synthesis of Wang-QTM (6)
Scheme 6
Scheme 6. Organocatalyzed Reductions of Nitroarenes 7a, 7f, and 7g with Wang-QTM/Wang-QTK
See this image and copyright information in PMC

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