Determining the origin of rate-independent chemoselectivity in CuAAC reactions: an alkyne-specific shift in rate-determining step

Ciaran P. Seath, Glenn A. Burley, Allan J. B. Watson

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Abstract

We report a kinetic and spectroscopic analysis of alkynedependent chemoselectivity in the copper-catalyzed azide-alkyne click (CuAAC) reaction. Studies of six alkyne subtypes reveal that the rate-determining step (RDS) of an aromatic ynamine class is shifted from acetylide formation to the azide ligation/migratory insertion event allowing chemoselectivity independent of overall rate.
Original languageEnglish
Pages (from-to)3314-3318
Number of pages5
JournalAngewandte Chemie International Edition
Volume56
Issue number12
Early online date16 Feb 2017
DOIs
Publication statusPublished - 13 Mar 2017

Keywords

  • kinetic analysis
  • spectroscopic analysis
  • chemoselectivity
  • copper-catalyzed azide-alkyne click
  • rate-determining step
  • aromatic ynamine class
  • acetylide formation
  • azide ligation
  • /migratory insertion

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