Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 1718-1724 |
| Number of pages | 7 |
| Journal | Organic Process Research and Development |
| Volume | 23 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - Aug 16 2019 |
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All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
A Convenient Preparation Method for Benzophenone Imine Catalyzed by Tetrabutylammonium Fluoride. / Kondo, Yuta; Morisaki, Kazuhiro; Hirazawa, Yoshinobu; Morimoto, Hiroyuki; Ohshima, Takashi.
In: Organic Process Research and Development, Vol. 23, No. 8, 16.08.2019, p. 1718-1724.Research output: Contribution to journal › Article
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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
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.
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U2 - 10.1021/acs.oprd.9b00226
DO - 10.1021/acs.oprd.9b00226
M3 - Article
VL - 23
SP - 1718
EP - 1724
JO - Organic Process Research and Development
JF - Organic Process Research and Development
SN - 1083-6160
IS - 8
ER -