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Title: Metal-free intermolecular azide-alkyne cycloaddition promoted by glycerol
Author: Rodriguez-Rodriguez, Marta
Gras, Emmanuel
Pericàs i Brondo, Miquel A. (Miquel Àngel)
Gómez, Montserrat
Keywords: Triazoles
Teoria del funcional de densitat
Reaccions de radicals lliures
Density functionals
Free radical reactions
Issue Date: 14-Dec-2015
Publisher: Wiley-VCH
Abstract: Metal-free intermolecular Huisgen cycloadditions using nonactivated internal alkynes have been successfully performed in neat glycerol, both under thermal and microwave dielectric heating. In sharp contrast, no reaction occurs in other protic solvents, such as water, ethanol, or diols. DFT calculations have shown that the BnN3/glycerol adduct promotes a more important stabilization of the corresponding LUMO than that produced in the analogous BnN3/alcohol adducts, favoring the reactivity with the alkyne in the first case. The presence of copper salts in the medium did not change the reaction pathway (Cu(I) acts as spectator), except for disubstituted silylalkynes, for which desilylation takes place in contrast to the metal-free system.
Note: Versió postprint del document publicat a:
It is part of: Chemistry-A European Journal, 2015, vol. 21, num. 51, p. 18706-18710
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ISSN: 0947-6539
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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