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Cu‐Catalyzed Chemoselective Reduction of N ‐Heteroaromatics with NH 3 · BH 3 in Aqueous Solution
Author(s) -
Gao Chao,
Xuan Qingqing,
Song Qiuling
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202100259
Subject(s) - chemistry , chemoselectivity , catalysis , aqueous solution , aqueous medium , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry
Main observation and conclusion An efficient catalytic system was successfully developed on reduction of N ‐heteroaromatics with H 3 N∙BH 3 as hydrogen source in CuSO 4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH‐, NH 2 ‐, 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 NH 3 ∙BH 3 , which was believed to form with H 3 N∙BH 3 in CuSO 4 solution.