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Aryldiazonium Salts as Nitrogen‐Based Lewis Acids: Facile Synthesis of Tuneable Azophosphonium Salts
Author(s) -
Habraken Evi R. M.,
van Leest Nicolaas P.,
Hooijschuur Pim,
de Bruin Bas,
Ehlers Andreas W.,
Lutz Martin,
Slootweg J. Chris
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201806913
Subject(s) - lewis acids and bases , chemistry , cyclic voltammetry , nitrogen , phosphine , electron transfer , base (topology) , organic chemistry , combinatorial chemistry , polymer chemistry , catalysis , electrochemistry , electrode , mathematical analysis , mathematics
Inspired by the commercially available azoimidazolium dyes (e.g., Basic Red 51) that can be obtained from aryldiazonium salts and N‐heterocyclic carbenes, we developed the synthesis of a unique set of arylazophosphonium salts. A range of colours were obtained by applying readily tuneable phosphine donor ligands and para ‐substituted aryldiazonium salts as nitrogen‐based Lewis acids. With cyclic voltammetry, a general procedure was designed to establish whether the reaction between a Lewis acid and a Lewis base occurs by single‐electron transfer or electron‐pair transfer.
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