Transition States of Strain-Promoted Metal-Free Click Chemistry:  1,3-Dipolar Cycloadditions of Phenyl Azide and Cyclooctynes

2008 ◽  
Vol 10 (8) ◽  
pp. 1633-1636 ◽  
Author(s):  
Daniel H. Ess ◽  
Gavin O. Jones ◽  
K. N. Houk
Keyword(s):  
Click Chemistry ◽  
Transition States ◽  
Phenyl Azide ◽  
Dipolar Cycloadditions ◽  
Metal Free

scholarly journals Chemoselective bioconjugation based on modular click chemistry with 4-halocoumarins and aryl sulfonates

RSC Advances ◽  
2021 ◽  
Vol 11 (31) ◽  
pp. 18960-18965
Author(s):  
F. Yushra Thanzeel ◽  
Christian Wolf
Keyword(s):  
Click Chemistry ◽  
Bond Formation ◽  
Metal Free

We report chemoselective and modular peptide bioconjugation using stoichiometric amounts of 4-halocoumarin and arylsulfonate agents that undergo metal-free C(sp2)-heteroatom bond formation at micromolar concentrations.

scholarly journals Functional modulation and directed assembly of an enzyme through designed non-natural post-translation modification

2015 ◽  
Vol 6 (7) ◽  
pp. 3712-3717 ◽  
Author(s):  
Andrew M. Hartley ◽  
Athraa J. Zaki ◽  
Adam R. McGarrity ◽  
Cecile Robert-Ansart ◽  
Andriy V. Moskalenko ◽  
...  
Keyword(s):  
Enzyme Activity ◽  
Click Chemistry ◽  
Directed Assembly ◽  
Phenyl Azide ◽  
Functional Modulation

Designed phenyl azide incorporation combined with bioorthogonal Click chemistry to regulate enzyme activity, or promote its stable assembly on graphene.

Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4501-4524 ◽  
Author(s):  
Jurij Svete ◽  
Uroš Grošelj ◽  
Franc Požgan ◽  
Bogdan Štefane
Keyword(s):  
Experimental Data ◽  
Click Chemistry ◽  
Organic Synthesis ◽  
Present Review ◽  
Metal Free ◽  
Azomethine Imine ◽  
Cuaac Reaction ◽  
Azomethine Imines

Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected examples of metal-free reactions, and related [3+3] and [3+4] cycloadditions of azomethine imines are presented. All these experimental data indicate the viability of CuAIAC in organic synthesis and the applicability in ‘click’ chemistry.1 Introduction2 Reactions with Acyclic Azomethine Imines3 Reactions with C,N-Cyclic Azomethine Imines4 Reactions with N,N-Cyclic Azomethine Imines5 Reactions with C,N,N-Cyclic Azomethine Imines6 The Mechanism of the CuAIAC Reaction7 Conclusions and Outlook

Phospha-Scorpionate Complexes by Click Chemistry using Phenyl Azide and Ethynylphosphine Oxides

2008 ◽  
Vol 27 (13) ◽  
pp. 3210-3215 ◽  
Author(s):  
Sander G. A. van Assema ◽  
Cornelis G. J. Tazelaar ◽  
G. Bas de Jong ◽  
Jan H. van Maarseveen ◽  
Marius Schakel ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Phenyl Azide
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