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

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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.

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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. https://doi.org/10.1002/anie.201612288

APA

Seath, C. P., Burley, G. A., & Watson, A. 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), 3314-3318. https://doi.org/10.1002/anie.201612288

Vancouver

Seath CP, Burley GA, Watson AJB. Determining the origin of rate-independent chemoselectivity in CuAAC reactions: an alkyne-specific shift in rate-determining step. Angewandte Chemie International Edition. 2017 Mar 13;56(12):3314-3318. https://doi.org/10.1002/anie.201612288

Author

Seath, Ciaran P. ; Burley, Glenn A. ; Watson, Allan J. B. / Determining the origin of rate-independent chemoselectivity in CuAAC reactions : an alkyne-specific shift in rate-determining step. In: Angewandte Chemie International Edition. 2017 ; Vol. 56, No. 12. pp. 3314-3318.

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@article{184be5384e8d49feb8d573a71f038d38,
title = "Determining the origin of rate-independent chemoselectivity in CuAAC reactions: an alkyne-specific shift in rate-determining step",
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.",
keywords = "Chemoselectivity, Click reactions, CuAAC, Reaction kinetics",
author = "Seath, {Ciaran P.} and Burley, {Glenn A.} and Watson, {Allan J. B.}",
note = "We thank the Carnegie Trust for a PhD Scholarship (C.P.S.), G.A.B. thanks the Alexander von Humboldt Foundation (Visiting Research Fellowship, LMU Munich).",
year = "2017",
month = mar,
day = "13",
doi = "10.1002/anie.201612288",
language = "English",
volume = "56",
pages = "3314--3318",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "John Wiley & Sons, Ltd.",
number = "12",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Determining the origin of rate-independent chemoselectivity in CuAAC reactions

T2 - an alkyne-specific shift in rate-determining step

AU - Seath, Ciaran P.

AU - Burley, Glenn A.

AU - Watson, Allan J. B.

N1 - We thank the Carnegie Trust for a PhD Scholarship (C.P.S.), G.A.B. thanks the Alexander von Humboldt Foundation (Visiting Research Fellowship, LMU Munich).

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 - Chemoselectivity

KW - Click reactions

KW - CuAAC

KW - Reaction kinetics

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 -

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