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Hydration and alkoxylation of alkynes catalyzed by NHC–Au–OTf

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Abstract

The NHC–Au–OTf [NHC = 1,3-bis(2,6-di-isopropylphenyl)-imidazol-2-ylidene] catalyst was tested in the alkoxylation and hydration of alkynes in a wide set of neoteric solvents for the first time. We found that most of these solvents (ethyl lactate, glycerol, propylene carbonate, D-limonene, γ-valerolactone, and p-cymene) are comparable or better solvents with respect to traditional VOSs. An important beneficial effect of γ-valerolactone was found in the hydration of inactive diphenylacetylene and one order of magnitude higher TOF was obtained with respect to the literature values. Kinetic experiments and DFT calculations seem to indicate that the polarity of the solvent and the presence of suitable proton acceptor/donor functionalities on the solvent itself could be taken into account.

Graphical abstract: Hydration and alkoxylation of alkynes catalyzed by NHC–Au–OTf

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Publication details

The article was received on 13 Feb 2018, accepted on 04 Apr 2018 and first published on 04 Apr 2018


Article type: Paper
DOI: 10.1039/C8GC00508G
Citation: Green Chem., 2018, Advance Article
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    Hydration and alkoxylation of alkynes catalyzed by NHC–Au–OTf

    M. Gatto, W. Baratta, P. Belanzoni, L. Belpassi, A. Del Zotto, F. Tarantelli and D. Zuccaccia, Green Chem., 2018, Advance Article , DOI: 10.1039/C8GC00508G

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