Premium
Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen
Author(s) -
Pastýříková Tereza,
Iakobson George,
Vida Norbert,
Pohl Radek,
Beier Petr
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200127
Subject(s) - chemistry , amination , aniline , nitro , benzene , yield (engineering) , medicinal chemistry , nucleophilic substitution , organic chemistry , catalysis , alkyl , materials science , metallurgy
1‐Nitro‐4‐(pentafluorosulfanyl)benzene underwent direct amination with 1,1,1‐trimethylhydrazinium iodide in the presence of t BuOK in DMSO to give 2‐nitro‐5‐(pentafluorosulfanyl)aniline in good yield. 1‐Nitro‐3‐(pentafluorosulfanyl)benzene, under similar conditions, gave 2‐nitro‐4‐(pentafluorosulfanyl)aniline, also in good yield. Reduction of either product with hydrogen in the presence of Raney nickel provided 4‐(pentafluorosulfanyl)benzene‐1,2‐diamine, which served as a precursor for the efficient synthesis of SF 5 ‐containing benzimidazoles, quinoxalines, and benzotriazoles.