908103-13-9Relevant academic research and scientific papers
Ruthenium-catalyzed tertiary amine formation from nitroarenes and alcohols
Feng, Chao,Liu, Yong,Peng, Shengming,Shuai, Qi,Deng, Guojun,Li, Chao-Jun
, p. 4888 - 4891 (2010)
A highly selective ruthenium-catalyzed C-N bond formation was developed by using the hydrogen-borrowing strategy. Various tertiary amines were obtained efficiently from nitroarenes and primary alcohols. The reaction tolerates a wide range of functionalities. A tentative mechanism was proposed for this direct amination reaction of alcohols with nitroarenes.
Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
supporting information, p. 15117 - 15127 (2021/10/25)
A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions
Li, Chao,Wan, Ke-Feng,Guo, Fu-Ya,Wu, Qian-Hui,Yuan, Mao-Lin,Li, Rui-Xiang,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua
, p. 2158 - 2168 (2019/05/16)
Herein, an efficient and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by the same catalytic system. Deuterium-labeling experiments and a series of control experiments were conducted, and the results suggested that an intermolecular borrowing hydrogen pathway might exist in the alkylation process.
Direct one-pot reductive N-alkylation of nitroarenes by using alcohols with supported gold catalysts
Tang, Chun-Hong,He, Lin,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian
supporting information; experimental part, p. 7172 - 7177 (2011/09/15)
Gold standard support! The direct reductive mono- or di-N-alkylation of aromatic nitro compounds with alcohols, using a hydrogen-borrowing strategy, was efficiently promoted by a ligand-free titania-supported gold catalyst system (see scheme). A variety of nitroarenes were selectively converted into the corresponding secondary or tertiary amines in good to excellent yields without any co-catalysts, such as bases and stabilizing ligands. Copyright
Selective N-alkylation of amines with alcohols by using non-metal-based acid-base cooperative catalysis
Du, Ya,Oishi, Shunsuke,Saito, Susumu
supporting information; experimental part, p. 12262 - 12267 (2011/11/29)
Learning to cooperate: A straightforward method for the selective N-mono- and dialkylation of amines with alcohols by means of non-metal-based catalysis promoted by TAPC is reported (see scheme). Selectivity of the N-mono- and dialkylation, substrate scope and functional-group tolerance are highlighted with respect to each amine (1° and 2°; aromatic and aliphatic) and alcohol (1°, 2° and 3°; benzylic and aliphatic) component. Copyright
