Chemoselective sequential click ligations directed by enhanced reactivity of an aromatic ynamine

Marine Z. C. Hatit, Joanna C. Sadler, Liam A. McLean, Benjamin C. Whitehurst, Ciaran P. Seath, Luke D. Humphreys, Robert J. Young, Allan J. B. Watson, Glenn A. Burley

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 +2] cycloaddition (“click”) reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethynylbenzimidazole is further demonstrated by the sequential click ligation of a series of highly functionalized azides using a heterobifunctional diyne, dispelling the need for alkyne protecting groups.
LanguageEnglish
Pages1694-1697
Number of pages4
JournalOrganic Letters
Volume18
Issue number7
Early online date22 Mar 2016
DOIs
Publication statusPublished - 1 Apr 2016

Fingerprint

Alkynes
alkynes
Ligation
reactivity
Triazoles
Azides
Cycloaddition
Cycloaddition Reaction
cycloaddition
Substrates
profiles

Keywords

  • N-Alkynylheteroarenes
  • N-ethynylbenzimidazole
  • sequential click ligation

Cite this

Hatit, Marine Z. C. ; Sadler, Joanna C. ; McLean, Liam A. ; Whitehurst, Benjamin C. ; Seath, Ciaran P. ; Humphreys, Luke D. ; Young, Robert J. ; Watson, Allan J. B. ; Burley, Glenn A. / Chemoselective sequential click ligations directed by enhanced reactivity of an aromatic ynamine. In: Organic Letters. 2016 ; Vol. 18, No. 7. pp. 1694-1697.
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abstract = "Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 +2] cycloaddition (“click”) reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethynylbenzimidazole is further demonstrated by the sequential click ligation of a series of highly functionalized azides using a heterobifunctional diyne, dispelling the need for alkyne protecting groups.",
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Chemoselective sequential click ligations directed by enhanced reactivity of an aromatic ynamine. / Hatit, Marine Z. C.; Sadler, Joanna C.; McLean, Liam A.; Whitehurst, Benjamin C.; Seath, Ciaran P.; Humphreys, Luke D.; Young, Robert J.; Watson, Allan J. B.; Burley, Glenn A.

In: Organic Letters, Vol. 18, No. 7, 01.04.2016, p. 1694-1697.

Research output: Contribution to journalArticle

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AU - Hatit, Marine Z. C.

AU - Sadler, Joanna C.

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AB - Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 +2] cycloaddition (“click”) reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethynylbenzimidazole is further demonstrated by the sequential click ligation of a series of highly functionalized azides using a heterobifunctional diyne, dispelling the need for alkyne protecting groups.

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