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An organoantimony nitrate complex with azastibocine framework as water tolerant Lewis acid catalyst for the synthesis of 1,2‐disubstitued benzimidazoles
Author(s) -
Zhou Cong,
Lei Jian,
Liu Yongping,
Au ChakTong,
Chen Yi,
Yin ShuangFeng
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5881
Subject(s) - chemistry , lewis acids and bases , catalysis , benzimidazole , lewis acid catalysis , cyan , organic chemistry , reusability , furfural , polymer chemistry , art , software , computer science , visual arts , programming language
A novel organoantimony complex of 6‐cyclohexyl‐6,7‐dihydrodibenzo[ c,f ] [ 1,5 ]azastibocin‐12(5H)‐yl nitrate ( 2 ) was synthesized and systematically characterized by techniques such as NMR spectra, TG‐DSC, and X‐ray diffraction. It was found that the complex 2 exhibits relatively strong Lewis acidity (3.3 < Ho ≤ 4.8) and could be employed as a water tolerant Lewis acid catalyst for the synthesis of synthetically valuable benzimidazole derivatives starting from aldehydes and arylenediamines. This catalytic system shows excellent tolerance toward a wide variety of functional groups, such as methyl, methoxyl, fluoro, chloro, bromo, nitro, cyan, trifluoromethyl, 1‐naphthaldehyde, furfural and n ‐butyl, together with facile reusability in 5 times scale enlarged synthesis.