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Brønsted Acid Promoted Reduction of Tertiary Phosphine Oxides
Author(s) -
Krachko Tetiana,
Lyaskovskyy Volodymyr,
Lutz Martin,
Lammertsma Koop,
Slootweg J. Chris
Publication year - 2017
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201700125
Subject(s) - triphenylphosphine , triphenylphosphine oxide , phosphine , triflic acid , brønsted–lowry acid–base theory , adduct , chemistry , phosphine oxide , phosphoric acid , oxide , catalysis , medicinal chemistry , organic chemistry
Recently, Brønsted acids, such as phosphoric acids, carboxylic acids, and triflic acid, were found to catalyze the reduction of phosphine oxides to the corresponding phosphines. In this study, we fully characterize the HCl, HOTf, and Me 2 SiHOTf adducts of triphenylphosphine oxide and find that the thermally stable adduct Ph 3 POH + OTf – is efficiently converted into triphenylphosphine at 100 °C in the presence of readily available hydrosiloxanes. Under the same reaction conditions, also Ph 3 POSiMe 2 H + OTf – selectively affords triphenylphosphine indicating that silylated phosphine oxides are likely intermediates in this process.