Alkyne-azide reactions

Sanne Schoffelen; Morten Peter Meldal

doi:10.1002/9783527677894.ch5

Alkyne-azide reactions

Sanne Schoffelen, Morten Peter Meldal

Kemisk Institut

9 Citationer (Scopus)

Abstract

The fundamental aspects and mechanism of the CuAAC click reaction, introduced by Tornøe and Meldal in 2001, is reviewed in great detail. Based on mechanistic considerations the influence of substrates, Cu(1) ligands and conditions e.g. concentration, polarity, inertness and temperature on the outcome of click reactions is evaluated. The most recently discovered and highly active catalysts based on NHC-ligands are discussed and compared with the traditional CuAAC-ligands. In situ and spatially controled click reactions are described and optimal click conditions provided. Finally the recent positive results of using CuAAC in biolabeling studies is discussed and the future perspective for this important field is outlined.

Originalsprog	Engelsk
Titel	Modern alkyne chemistry : catalytic and atom-economic transformations
Redaktører	Barry M. Trost, Chao-Jun Li
Antal sider	28
Forlag	Wiley-VCH
Publikationsdato	9 feb. 2015
Sider	115-142
Kapitel	5
ISBN (Trykt)	978-3-527-33505-3
ISBN (Elektronisk)	978-3-527-67790-0
DOI	https://doi.org/10.1002/9783527677894.ch5
Status	Udgivet - 9 feb. 2015

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10.1002/9783527677894.ch5

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abstract = "The fundamental aspects and mechanism of the CuAAC click reaction, introduced by Torn{\o}e and Meldal in 2001, is reviewed in great detail. Based on mechanistic considerations the influence of substrates, Cu(1) ligands and conditions e.g. concentration, polarity, inertness and temperature on the outcome of click reactions is evaluated. The most recently discovered and highly active catalysts based on NHC-ligands are discussed and compared with the traditional CuAAC-ligands. In situ and spatially controled click reactions are described and optimal click conditions provided. Finally the recent positive results of using CuAAC in biolabeling studies is discussed and the future perspective for this important field is outlined.",

keywords = "click reaction, CuAAC, mechanism, click optimization, solvent effect, catalysis, click ligands, Bio-labeling, Cu free",

author = "Sanne Schoffelen and Meldal, {Morten Peter}",

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language = "English",

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T1 - Alkyne-azide reactions

AU - Schoffelen, Sanne

AU - Meldal, Morten Peter

PY - 2015/2/9

Y1 - 2015/2/9

N2 - The fundamental aspects and mechanism of the CuAAC click reaction, introduced by Tornøe and Meldal in 2001, is reviewed in great detail. Based on mechanistic considerations the influence of substrates, Cu(1) ligands and conditions e.g. concentration, polarity, inertness and temperature on the outcome of click reactions is evaluated. The most recently discovered and highly active catalysts based on NHC-ligands are discussed and compared with the traditional CuAAC-ligands. In situ and spatially controled click reactions are described and optimal click conditions provided. Finally the recent positive results of using CuAAC in biolabeling studies is discussed and the future perspective for this important field is outlined.

AB - The fundamental aspects and mechanism of the CuAAC click reaction, introduced by Tornøe and Meldal in 2001, is reviewed in great detail. Based on mechanistic considerations the influence of substrates, Cu(1) ligands and conditions e.g. concentration, polarity, inertness and temperature on the outcome of click reactions is evaluated. The most recently discovered and highly active catalysts based on NHC-ligands are discussed and compared with the traditional CuAAC-ligands. In situ and spatially controled click reactions are described and optimal click conditions provided. Finally the recent positive results of using CuAAC in biolabeling studies is discussed and the future perspective for this important field is outlined.

KW - click reaction, CuAAC, mechanism, click optimization, solvent effect, catalysis, click ligands, Bio-labeling, Cu free

U2 - 10.1002/9783527677894.ch5

DO - 10.1002/9783527677894.ch5

M3 - Book chapter

SN - 978-3-527-33505-3

SP - 115

EP - 142

BT - Modern alkyne chemistry

A2 - Trost, Barry M.

A2 - Li, Chao-Jun

PB - Wiley-VCH

ER -

Alkyne-azide reactions

Abstract

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