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

Heejin Kim, Yuya Yonekura, Jun Ichi Yoshida

Research output: Contribution to journalArticle

13 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

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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