51004-00-3Relevant articles and documents
A Convenient Preparation Method for Benzophenone Imine Catalyzed by Tetrabutylammonium Fluoride
Kondo, Yuta,Morisaki, Kazuhiro,Hirazawa, Yoshinobu,Morimoto, Hiroyuki,Ohshima, Takashi
, p. 1718 - 1724 (2019)
Benzophenone imine is a useful ammonia equivalent in the Buchwald-Hartwig amination and an important intermediate for the synthesis of N-protected primary amines. However, the conventional synthesis of benzophenone imine requires stoichiometric amounts of metal reagents or high-pressure conditions. Herein we report a facile method for preparing benzophenone imine to enhance its potential utility. The reaction is performed by mixing commercially available benzophenone and bis(trimethylsilyl)amine in the presence of a catalytic amount of tetrabutylammonium fluoride at ambient temperature and pressure and can be readily applied to a multigram-scale synthesis even in a standard academic laboratory setup. Preliminary mechanistic studies and the application of the reaction to one-pot benzophenone imine synthesis/Buchwald-Hartwig amination are also reported.
Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines
Hirazawa, Yoshinobu,Kadota, Tetsuya,Kondo, Yuta,Morimoto, Hiroyuki,Morisaki, Kazuhiro,Ohshima, Takashi
, p. 120 - 125 (2020/02/20)
N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.
Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C?O and C?C Bond Activation
Yue, Huifeng,Guo, Lin,Liao, Hsuan-Hung,Cai, Yunfei,Zhu, Chen,Rueping, Magnus
supporting information, p. 4282 - 4285 (2017/04/03)
An efficient nickel-catalyzed decarbonylative amination reaction of aryl and heteroaryl esters has been achieved for the first time. The new amination protocol allows the direct interconversion of esters and amides into the corresponding amines and represents a good alternative to classical rearrangements as well as cross coupling reactions.
