Chemoselective Nitro Reduction Using Nitrogen‐Doped Carbon‐Encapsulated Ni Catalyst and Y‐Type Packed Bed Column for Continuous Flow Reaction

• Published in: Advanced synthesis & catalysis Vol. 365; no. 13; pp. 2230 - 2239
• Main Authors: Cao, Lei, Asad Abbas, Syed, Hyeon Jeong, Seo, Seo, Dongho, Min Nam, Ki, Kyoon Park, Jin
• Format: Journal Article
• Language: English
• Published: Heidelberg Wiley Subscription Services, Inc 04-07-2023
• Subjects: Amines; Aromatic compounds; Carbon; Catalysts; Chemoselective; Continuous flow; Flow chemistry; Heterogeneous catalysis; Nitro reduction; Nitrogen; Osimertinib; Packed beds; Room temperature; Silica gel
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202300357

Selective reduction of nitro‐containing arenes and heteroarenes was achieved in 5 minutes at room temperature utilizing inexpensive NaBH4 as a hydrogen source and a newly developed Ni@N−C catalyst, obtained via a simple carbon coating process without the need for an external carbon source. A wide variety of nitro derivatives, including pharmaceutical molecules, was successfully reduced to the corresponding amines in yields ranging from 45% to 99% using the Ni@N−C catalyst under general batch conditions. The reactivity and selectivity of the nitro reduction were further enhanced by a continuous flow reaction system, especially when a newly designed Y‐type column was used, and the Osimertinib intermediate was produced on gram scale after 24 hours without any nickel metal contamination or silica gel chromatography purification.