A Catalyst-Free Amination of Functional Organolithium Reagents by Flow Chemistry

Heejin Kim, Yuya Yonekura, Jun Ichi Yoshida

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

Reported is the electrophilic amination of functional organolithium intermediates with well-designed aminating reagents under mild reaction conditions using flow microreactors. The aminating reagents were optimized to achieve efficient C−N bond formation without using any catalyst. The electrophilic amination reactions of functionalized aryllithiums were successfully conducted under mild reaction conditions, within 1 minute, by using flow microreactors. The aminating reagent was also prepared by the flow method. Based on stopped-flow NMR analysis, the reaction time for the preparation of the aminating reagent was quickly optimized without the necessity of work-up. Integrated one-flow synthesis consisting of the generation of an aryllithium, the preparation of an aminating reagent, and their combined reaction was successfully achieved to give the desired amine within 5 minutes of total reaction time.

Original languageEnglish
Pages (from-to)4063-4066
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number15
DOIs
Publication statusPublished - 2018 Apr 3
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported by Grant-in-Aid for Scientific Research (S) 26220804 and Grant-in-Aid for Young Scientists (B) 16K17898 funded by Japan Society for the Promotion of Science (JSPS). We also thank Dr. Bertram Manz, Magritek Ltd. and Mr. Aritaka Kaneyama, Asahi Lab Commerce, Inc. for use of their Spinsolve benchtop NMR instrument.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • NMR spectroscopy
  • amination
  • flow chemistry
  • microreactors
  • organolithiums

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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