Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 39, Issue 9, Pages 2504-2508Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202100259
Keywords
Nitrogen heterocycles; NH3; BH3; Hydrogen transfer; [Cu-H] intermediate; Chemoselectivity
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Funding
- National Natural Science Foundation of China [21702065, 21772046, 2193103]
- Promotion Program for Young and Middle-aged Teacher in Science and Technology Research of Huaqiao University
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Efficient catalytic system using H3N·BH3 as the hydrogen source in CuSO4 solution was developed for the reduction of N-heteroaromatics, showing excellent chemoselectivity and broad functional group tolerance. Various challenging substrates were smoothly reduced, possibly via the generation of [Cu-H] intermediate in the reaction.
Main observation and conclusion An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N center dot BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3 center dot BH3, which was believed to form with H3N center dot BH3 in CuSO4 solution.
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