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Issue 3, 2016
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Development of silica-supported frustrated Lewis pairs: highly active transition metal-free catalysts for the Z-selective reduction of alkynes

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Abstract

Supported Lewis acid/base systems based on a triphenyl phosphine fragment and Piers' reagent (HB(C6F5)2) or BArF have been prepared and characterized. Both materials show unprecedented catalytic activity in the Z-selective hydrogenation of 3-hexyne to Z-3-hexene with a selectivity up to 87%. Other alkynes can also be hydrogenated Z-selectively, albeit with moderate yields. The activity of the supported phosphine/HB(C6F5)2 adduct is similar to the only homogeneous example reported thus far based on bridged B/N frustrated Lewis pairs under high hydrogen pressure. Importantly, this transition metal-free supported catalyst was recycled five times in the challenging selective hydrogenation of a non-polar unactivated alkyne.

Graphical abstract: Development of silica-supported frustrated Lewis pairs: highly active transition metal-free catalysts for the Z-selective reduction of alkynes

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Publication details

The article was received on 20 Aug 2015, accepted on 05 Oct 2015 and first published on 08 Oct 2015


Article type: Paper
DOI: 10.1039/C5CY01372K
Author version available: Download Author version (PDF)
Citation: Catal. Sci. Technol., 2016,6, 882-889
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    Development of silica-supported frustrated Lewis pairs: highly active transition metal-free catalysts for the Z-selective reduction of alkynes

    K. C. Szeto, W. Sahyoun, N. Merle, J. L. Castelbou, N. Popoff, F. Lefebvre, J. Raynaud, C. Godard, C. Claver, L. Delevoye, R. M. Gauvin and M. Taoufik, Catal. Sci. Technol., 2016, 6, 882
    DOI: 10.1039/C5CY01372K

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