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Updated: Aug 22, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Bis(amidophenolato)phosphonium: Si-H Hydride Abstraction and Phosphorus-Ligand Cooperative Activation of C-C Multiple
Daniel Roth1, Thaddäus Thorwart1, Clara Douglas1,2
1Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Abstract:
The first bis(amidophenolato)phosphonium salts are prepared and fully characterized. The perfluorinated derivative represents the strongest monocationic phosphorus Lewis acid on the fluoride and hydride ion affinity scale isolable to date. This affinity enables new reactions, such as hydride abstraction from Et3 SiH, the first phosphaalkoxylation of an alkyne or a phosphorus catalyzed intramolecular hydroarylation. All properties and reactions are scrutinized by theory and experiment. Substantial σ- and π-acidity provides the required affinity for substrate activation, while phosphorus-ligand cooperativity substantially enriches the reactivity portfolio of phosphonium ions.
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