Facile synthesis of enol ethers via Zn(OTf)2-mediated formal alkyne hydration-Smiles rearrangement

RSC Advances ◽  
2014 ◽  
Vol 4 (32) ◽  
pp. 16765-16768 ◽  
Author(s):  
Xinying Chew ◽  
Yuhan Lin ◽  
Yee Hwee Lim
Keyword(s):  
Terminal Alkynes ◽  
Facile Synthesis ◽  
Smiles Rearrangement ◽  
Enol Ethers

Terminal alkynes can be chemoselectively transformed into enol ethers via a formal tandem Markovnikov hydration-Smiles type rearrangement using Zn(OTf)2.

Facile synthesis of enol ethers by cleavage of α-bromoacetals and α-bromoketals mediated by SmI2

2001 ◽  
Vol 42 (22) ◽  
pp. 3729-3732 ◽  
Author(s):  
Heui Sul Park ◽  
Seong Ho Kim ◽  
Min Young Park ◽  
Yong Hae Kim
Keyword(s):  
Facile Synthesis ◽  
Enol Ethers

scholarly journals Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

2020 ◽  
Vol 16 ◽  
pp. 1683-1692 ◽  
Author(s):  
Dominik Göbel ◽  
Marius Friedrich ◽  
Enno Lork ◽  
Boris J Nachtsheim
Keyword(s):  
High Efficiency ◽  
Photophysical Properties ◽  
Covalent Attachment ◽  
Terminal Alkynes ◽  
Facile Synthesis ◽  
Triazole Derivatives ◽  
Emission Behavior ◽  
Substituted Benzaldehydes ◽  
Covalently Linked

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.

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