Chemoselective Reductions of Nitroaromatics in Water at Room Temperature

Sean M. Kelly and Bruce H. Lipshutz*

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: lipshutzchem.ucsb.edu

S. M. Kelly, B. H. Lipshutz, Org. Lett., 2014, 16, 98-101.

DOI: 10.1021/ol403079x

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Abstract

A robust and green protocol for the reduction of functionalized nitroarenes to the corresponding primary amines relies on inexpensive zinc dust in water containing nanomicelles derived from the commercially available designer surfactant TPGS-750-M. This mild process takes place at room temperature and tolerates a wide range of functionalities including common protecting groups.

see article for more examples

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High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

X. Li, R. R. Thakore, B. S. Takale, F. Gallou, B. H. Lipshutz, Org. Lett., 2021, 23, 8114-8118.

Carbonyl Iron Powder: A Reagent for Nitro Group Reductions under Aqueous Micellar Catalysis Conditions

N. R. Lee, A. A. Bikovtseva, M. Cortes-Clerget, F. Gallou, B. H. Lipshutz, Org. Lett., 2017, 19, 6518-6521.

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Key Words

Reduction of Nitro Compounds, Zinc, Green Chemistry

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ID: J54-Y2014