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

Hatit, Marine Z. C. and Seath, Ciaran P. and Watson, Allan J. B. and Burley, Glenn A. (2017) A strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine. Journal of Organic Chemistry. ISSN 0022-3263 (https://doi.org/10.1021/acs.joc.7b00545)

[thumbnail of Hatit-etal-JOC2017-A-strategy-for-conditional-orthogonal-sequential-CuAAC]
Preview
 Text. Filename: Hatit_etal_JOC2017_A_strategy_for_conditional_orthogonal_sequential_CuAAC.pdf
Accepted Author Manuscript
Download (623kB)| Preview

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.

ORCID iDs

Hatit, Marine Z. C. ORCID logoORCID: https://orcid.org/0000-0002-5713-6596, Seath, Ciaran P. ORCID logoORCID: https://orcid.org/0000-0002-6774-128X, Watson, Allan J. B. and Burley, Glenn A.;
  • Item type:Article
    ID code:60572
    Dates:
    Date
    Event
    28 April 2017
    Published
    28 April 2017
    Published Online
    28 April 2017
    Accepted
    Notes: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.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Technology and Innovation Centre > Bionanotechnology
    Depositing user: Pure Administrator
    Date deposited:03 May 2017 11:10
    Last modified:11 Nov 2024 11:41
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/60572
CORE (COnnecting REpositories)