42834-19-5Relevant articles and documents
Copper-Catalysed Electrophilic Amination of Aryl(alkenyl) Boronic Acids with Nitrogen-Containing Hypervalent Iodine (III) Reagent
Hu, Yuanyuan,Zheng, Songlin,Fan, Wu,Yuan, Weiming
supporting information, p. 4701 - 4707 (2021/08/23)
A copper-catalysed electrophilic N-imination of aryl(alkenyl) boronic acids with a stable hypervalent iodine(III) reagent containing a transferable (diarylmethylene)amino group is developed. The electrophilic C?N cross-coupling reaction proceeds smoothly at room temperature under oxidant-free and base-free conditions, which is further characterized by the broad functional group compatibility, thereof, extending the N-electrophile scope of electrophilic C?N cross-coupling outside the limitation of N?O and N?Cl reagents. (Figure presented.).
A Convenient Preparation Method for Benzophenone Imine Catalyzed by Tetrabutylammonium Fluoride
Kondo, Yuta,Morisaki, Kazuhiro,Hirazawa, Yoshinobu,Morimoto, Hiroyuki,Ohshima, Takashi
, p. 1718 - 1724 (2019/09/06)
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.
Oxidative Rearrangement of Primary Amines Using PhI(OAc)2 and Cs2CO3
Yamakoshi, Wataru,Arisawa, Mitsuhiro,Murai, Kenichi
supporting information, (2019/05/08)
An oxidative rearrangement of primary amines mediated by a hypervalent iodine(III) reagent is herein reported. The combination of PhI(OAc)2 and Cs2CO3 proves highly efficient at inducing the direct 1,2-C to N migration of primary amines, which can be applied to the preparation of both acyclic and cyclic amines. A mechanistic study shows that the rearrangement proceeds via a concerted mechanism.