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

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.

authors

• Gabbai, Francois

published proceedings

• Dalton Trans

altmetric score

• 5.3

author list (cited authors)

• Yang, M., Hirai, M., & Gabbai, F. P.

citation count

• 39

complete list of authors

• Yang, Mengxi||Hirai, Masato||Gabbaiï, François P

publication date

• May 2019

publisher

• Royal Society of Chemistry (RSC)  Publisher

published in

• Dalton Transactions  Journal

keywords

• Antimony
• Benzene Derivatives
• Borates
• Catalysis
• Cations
• Hydrogenation
• Lewis Acids
• Molecular Structure
• Organometallic Compounds
• Organophosphorus Compounds
• Phosphines
• Quinolines
• Stereoisomerism
• Structure-Activity Relationship

PubMed Central ID

• 30997474

Digital Object Identifier (DOI)

• 10.1039/c9dt01357a

start page

• 6685

end page

• 6689

volume

• 48

issue

• 20

URL

• http://dx.doi.org/10.1039/c9dt01357a