Abstract
Language | English |
---|---|
Pages | 3314-3318 |
Number of pages | 5 |
Journal | Angewandte Chemie International Edition |
Volume | 56 |
Issue number | 12 |
Early online date | 16 Feb 2017 |
DOIs | |
Publication status | Published - 13 Mar 2017 |
Fingerprint
Keywords
- kinetic analysis
- spectroscopic analysis
- chemoselectivity
- copper-catalyzed azide-alkyne click
- rate-determining step
- aromatic ynamine class
- acetylide formation
- azide ligation
- /migratory insertion
Cite this
}
Determining the origin of rate-independent chemoselectivity in CuAAC reactions : an alkyne-specific shift in rate-determining step. / Seath, Ciaran P.; Burley, Glenn A.; Watson, Allan J. B.
In: Angewandte Chemie International Edition, Vol. 56, No. 12, 13.03.2017, p. 3314-3318.Research output: Contribution to journal › Article
TY - JOUR
T1 - Determining the origin of rate-independent chemoselectivity in CuAAC reactions
T2 - Angewandte Chemie International Edition
AU - Seath, Ciaran P.
AU - Burley, Glenn A.
AU - Watson, Allan J. B.
N1 - 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.
PY - 2017/3/13
Y1 - 2017/3/13
N2 - 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.
AB - 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.
KW - kinetic analysis
KW - spectroscopic analysis
KW - chemoselectivity
KW - copper-catalyzed azide-alkyne click
KW - rate-determining step
KW - aromatic ynamine class
KW - acetylide formation
KW - azide ligation
KW - /migratory insertion
UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773
U2 - 10.1002/anie.201612288
DO - 10.1002/anie.201612288
M3 - Article
VL - 56
SP - 3314
EP - 3318
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
IS - 12
ER -