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

Seath, Ciaran P. and Burley, Glenn A. and Watson, Allan J. B. (2017) Determining the origin of rate-independent chemoselectivity in CuAAC reactions : an alkyne-specific shift in rate-determining step. Angewandte Chemie International Edition, 56 (12). pp. 3314-3318. ISSN 1521-3773 (https://doi.org/10.1002/anie.201612288)

[thumbnail of Seath-etal-AWIE2017-Determining-the-origin-of-rate-independent-chemoselectivity]
Preview
 Text. Filename: Seath_etal_AWIE2017_Determining_the_origin_of_rate_independent_chemoselectivity.pdf
Accepted Author Manuscript
Download (922kB)| Preview

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.

ORCID iDs

Seath, Ciaran P. ORCID logoORCID: https://orcid.org/0000-0002-6774-128X, Burley, Glenn A. and Watson, Allan J. B.;
  • Item type:Article
    ID code:60227
    Dates:
    Date
    Event
    13 March 2017
    Published
    16 February 2017
    Published Online
    19 December 2016
    Accepted
    Notes:This is the peer reviewed version of the following article: Seath, CP, Burley, GA & Watson, AJB 2017, 'Determining the origin of rate-independent chemoselectivity in CuAAC reactions: an alkyne-specific shift in rate-determining step' Angewandte Chemie International Edition, vol 56, no. 12, pp. 3314-3318, which has been published in final form at http//dx.doi.org/10.1002/anie.201612288. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Technology and Innovation Centre > Bionanotechnology
    Depositing user: Pure Administrator
    Date deposited:16 Mar 2017 15:30
    Last modified:11 Nov 2024 11:37
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/60227
CORE (COnnecting REpositories)