Alkyne-azide cycloadditions with copper powder in a high-pressure continuous-flow reactor: High-temperature conditions versus the role of additives

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

A safe and efficient flow-chemistry-based procedure is presented for 1,3-dipolar cycloaddition reactions between organic azides and acetylenes. This simple and inexpensive technique eliminates the need for costly special apparatus and utilizes Cu powder as a plausible CuI source. To maximize the reaction rates, high-pressure/high-temperature conditions are utilized; alternatively, the harsh reaction conditions can be moderated at room temperature by the joint application of basic and acidic additives. A comparison of the performance of these two approaches in a series of model reactions has resulted in the formation of useful 1,4-disubstituted 1,2,3-triazoles in excellent yields. The risks that are associated with the handling of azides are lowered, thanks to the benefits of flow processing, and gram-scale production has been safely implemented. The synthetic capability of this continuous-flow technique is demonstrated by the efficient syntheses of some highly functionalized derivatives of the antifungal cispentacin. Alive and clicking: A simple, efficient, and safe continuous-flow procedure is presented for Cu I-catalyzed azide-alkyne cycloaddition reactions. The harsh reaction conditions that are required for high reaction rates can be moderated through the use of additives. The outstanding synthetic capabilities of this method are demonstrated by the efficient synthesis of some highly functionalized derivatives of the antifungal cispentacin.

Original languageEnglish
Pages (from-to)800-808
Number of pages9
JournalChemistry - An Asian Journal
Volume8
Issue number4
DOIs
Publication statusPublished - Apr 1 2013

Keywords

  • alkynes
  • azides
  • click chemistry
  • continuous-flow reactors
  • copper

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Alkyne-azide cycloadditions with copper powder in a high-pressure continuous-flow reactor: High-temperature conditions versus the role of additives'. Together they form a unique fingerprint.

  • Cite this