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

Xiaohan Li, Ruchita R. Thakore, Balaram S. Takale*, Fabrice Gallou and Bruce H. Lipshutz*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: balaram_takaleucsb.edu, bhlipshutzucsb.edu

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

DOI: 10.1021/acs.orglett.1c03258

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Abstract

Pd/C can be used as a catalyst for nitro group reductions at very low Pd loading either in the presence of triethylsilane as a transfer hydrogenating agent or simply using a hydrogen balloon. With this technology, a series of nitro compounds was reduced to the desired amines in high yields. Both the catalyst and surfactant were recycled several times without loss of activity.

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surfactant

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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.

Chemoselective Reductions of Nitroaromatics in Water at Room Temperature

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

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Key Words

Reduction of Nitro Compounds, Hydrogen, Green Chemistry

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ID: J54-Y2021