A Convenient Preparation Method for Benzophenone Imine Catalyzed by Tetrabutylammonium Fluoride

Yuta Kondo, Kazuhiro Morisaki, Yoshinobu Hirazawa, Hiroyuki Morimoto, Takashi Ohshima

研究成果: ジャーナルへの寄稿記事

抄録

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.

元の言語英語
ページ(範囲)1718-1724
ページ数7
ジャーナルOrganic Process Research and Development
23
発行部数8
DOI
出版物ステータス出版済み - 8 16 2019

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Imines
imines
fluorides
preparation
synthesis
Amination
amines
Amines
ambient temperature
reagents
ammonia
Ammonia
Metals
tetrabutylammonium
benzophenone
metals
Temperature

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

A Convenient Preparation Method for Benzophenone Imine Catalyzed by Tetrabutylammonium Fluoride. / Kondo, Yuta; Morisaki, Kazuhiro; Hirazawa, Yoshinobu; Morimoto, Hiroyuki; Ohshima, Takashi.

:: Organic Process Research and Development, 巻 23, 番号 8, 16.08.2019, p. 1718-1724.

研究成果: ジャーナルへの寄稿記事

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AU - Morimoto, Hiroyuki

AU - Ohshima, Takashi

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