TY - JOUR
T1 - A Convenient Preparation Method for Benzophenone Imine Catalyzed by Tetrabutylammonium Fluoride
AU - Kondo, Yuta
AU - Morisaki, Kazuhiro
AU - Hirazawa, Yoshinobu
AU - Morimoto, Hiroyuki
AU - Ohshima, Takashi
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas (JSPS KAKENHI Grant JP15H05846 in Middle Molecular Strategy to T.O.) and Grants-in-Aid for Scientific Research (B) (JSPS KAKENHI Grant JP17H03972 to T.O.) and (C) (JSPS KAKENHI Grant JP18K06581 to H.M.) from JSPS and Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS) (Grant JP18am0101091) from AMED. Y.K. and K.M. thank JSPS for Research Fellowships for Young Scientists. Y.K. is grateful for the support from the Academic Challenge Program 2018 of Kyushu University.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/8/16
Y1 - 2019/8/16
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85071537070&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85071537070&partnerID=8YFLogxK
U2 - 10.1021/acs.oprd.9b00226
DO - 10.1021/acs.oprd.9b00226
M3 - Article
AN - SCOPUS:85071537070
VL - 23
SP - 1718
EP - 1724
JO - Organic Process Research and Development
JF - Organic Process Research and Development
SN - 1083-6160
IS - 8
ER -