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

5 Citations (Scopus)

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.
LanguageEnglish
JournalJournal of Organic Chemistry
Early online date28 Apr 2017
DOIs
Publication statusE-pub ahead of print - 28 Apr 2017

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Alkynes
Azides
Cycloaddition

Keywords

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

Cite this

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title = "A strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine",
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 theynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.",
keywords = "Cu-catalyzed azide alkyne cycloaddition, aromatic ynamine, silyl deprotection",
author = "Hatit, {Marine Z. C.} and Seath, {Ciaran P.} and Watson, {Allan J. B.} and Burley, {Glenn A.}",
note = "This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright {\circledC} American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b00545.",
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A strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine. / Hatit, Marine Z. C.; Seath, Ciaran P.; Watson, Allan J. B.; Burley, Glenn A.

In: Journal of Organic Chemistry, 28.04.2017.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine

AU - Hatit, Marine Z. C.

AU - Seath, Ciaran P.

AU - Watson, Allan J. B.

AU - Burley, Glenn A.

N1 - This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b00545.

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N2 - 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 theynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.

AB - 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 theynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.

KW - Cu-catalyzed azide alkyne cycloaddition

KW - aromatic ynamine

KW - silyl deprotection

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