Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen

0376771 - ÚOCHB 2013 RIV DE eng J - Článek v odborném periodiku
Pastýříková, Tereza - Iakobson, George - Vida, Norbert - Pohl, Radek - Beier, Petr
Direct Amination of Nitro(pentafluorosulfanyl)benzenes through Vicarious Nucleophilic Substitution of Hydrogen.
European Journal of Organic Chemistry. -, č. 11 (2012), s. 2123-2126. ISSN 1434-193X. E-ISSN 1099-0690
Grant CEP: GA ČR GAP207/12/0072
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: sulfur * amination * nucleophilic substitution * nitrogen heterocycles
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 3.344, rok: 2012

1-Nitro-4-(pentafluorosulfanyl)benzene underwent direct amination with 1,1,1-trimethylhydrazinium iodide in the presence of tBuOK 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 SF5-containing benzimidazoles, quinoxalines, and benzotriazoles.
Trvalý link: http://hdl.handle.net/11104/0209089