A strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine

Marine Z. C. Hatit, Ciaran P. Seath, Allan J. B. Watson, Glenn A. Burley

Research output: Contribution to journalArticle

11 Citations (Scopus)
36 Downloads (Pure)

Abstract

A method for conditional control of orthogonal sequential Cu-catalyzed azide alkyne cycloaddition (CuAAC) reactions is reported. The inherent reactivity of an aromatic ynamine is controlled by a silyl protecting group that allows the selective CuAAC reaction of less reactive alkynes. Alternatively, the same protected ynamine undergoes selective CuAAC reaction via silyl deprotection in situ to give the
ynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.
Original languageEnglish
JournalJournal of Organic Chemistry
Early online date28 Apr 2017
DOIs
Publication statusE-pub ahead of print - 28 Apr 2017

Keywords

  • Cu-catalyzed azide alkyne cycloaddition
  • aromatic ynamine
  • silyl deprotection

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