133317-05-2Relevant academic research and scientific papers
Silver(I)-mediated regioselective oxidative cross-coupling of phenol and aniline derivatives resulting in 2′-aminobiphenyl-2-ols
Berkessa, Sololiya C.,Clarke, Zachary J.F.,Fotie, Jean,Bohle, D. Scott,Grimm, Casey C.
supporting information, p. 1613 - 1618 (2018/03/29)
A broad and efficient regioselective aerobic oxidative cross-coupling of phenols and aniline derivatives in the presence of AgNO3 and H2O2 resulting in 2′-aminobiphenyl-2-ols has been developed. This reaction is selective toward the creation of a new C–C bond at the ortho position to both amine and hydroxyl functional groups in the respective starting materials. Although oxidative cross-coupling of phenols and anilines resulting in 2′-aminobiphenyl-2-ol derivatives have been reported, these reactions have been mainly limited to 2-naphthol and 1-naphthol. This is one of the rare reports in which this type of cross-coupling reaction is expanded to simple phenol derivatives.
Selective N-alkylation of amines using nitriles under hydrogenation conditions: Facile synthesis of secondary and tertiary amines
Ikawa, Takashi,Fujita, Yuki,Mizusaki, Tomoteru,Betsuin, Sae,Takamatsu, Haruki,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
supporting information; experimental part, p. 293 - 304 (2012/02/01)
Nitriles were found to be highly effective alkylating reagents for the selective N-alkylation of amines under catalytic hydrogenation conditions. For the aromatic primary amines, the corresponding secondary amines were selectively obtained under Pd/C-catalyzed hydrogenation conditions. Although the use of electron poor aromatic amines or bulky nitriles showed a lower reactivity toward the reductive alkylation, the addition of NH4OAc enhanced the reactivity to give secondary aromatic amines in good to excellent yields. Under the same reaction conditions, aromatic nitro compounds instead of the aromatic primary amines could be directly transformed into secondary amines via a domino reaction involving the one-pot hydrogenation of the nitro group and the reductive alkylation of the amines. While aliphatic amines were effectively converted to the corresponding tertiary amines under Pd/C-catalyzed conditions, Rh/C was a highly effective catalyst for the N-monoalkylation of aliphatic primary amines without over-alkylation to the tertiary amines. Furthermore, the combination of the Rh/C-catalyzed N-monoalkylation of the aliphatic primary amines and additional Pd/C-catalyzed alkylation of the resulting secondary aliphatic amines could selectively prepare aliphatic tertiary amines possessing three different alkyl groups. According to the mechanistic studies, it seems reasonable to conclude that nitriles were reduced to aldimines before the nucleophilic attack of the amine during the first step of the reaction.
