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Issue 20, 2019
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Phosphonium–stibonium and bis-stibonium cations as pnictogen-bonding catalysts for the transfer hydrogenation of quinolines

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Abstract

Bifunctional Lewis acidic group 15 compounds have emerged as appealing platforms for anion sensing and organocatalysis. As part of our interest in the chemistry of these compounds, we have now compared the catalytic properties of [o-(MePPh2)C6H4SbPh2]+ ([3]+), [o-(PPh2)C6H4SbPh3]+ ([4]+), [o-(MePPh2)C6H4SbPh3]2+ ([5]2+), and [o-C6H4(SbMePh2)2]2+ ([6]2+) using the transfer hydrogenation of 2-phenyl-quinoline and 3-bromoquinoline with a Hantzsch ester benchmark reactions. This study, which also involved an evaluation of the catalytic properties of [Ph4Sb]+ and [Ph3MeP]+, shows that antimony cations are generally more active than their phosphorus counterparts and neutral stiboranes. Our results also demonstrate that dicationic systems such as [6]2+ are superior activators.

Graphical abstract: Phosphonium–stibonium and bis-stibonium cations as pnictogen-bonding catalysts for the transfer hydrogenation of quinolines

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Supplementary files

Article information


Submitted
29 Mar 2019
Accepted
01 Apr 2019
First published
01 Apr 2019

Dalton Trans., 2019,48, 6685-6689
Article type
Communication

Phosphonium–stibonium and bis-stibonium cations as pnictogen-bonding catalysts for the transfer hydrogenation of quinolines

M. Yang, M. Hirai and F. P. Gabbaï, Dalton Trans., 2019, 48, 6685
DOI: 10.1039/C9DT01357A

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