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Rapid Metal‐Free Formation of Free Phosphines from Phosphine Oxides
Author(s) -
ProvisEvans Cei B.,
Emanuelsson Emma A. C.,
Webster Ruth L.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800723
Subject(s) - borane , chemistry , phosphine , pinacol , reagent , reducing agent , sulfide , tetrahydrofuran , catalysis , organic chemistry , combinatorial chemistry , photochemistry , inorganic chemistry , solvent
A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as borane tetrahydrofuran complex (BH 3 ⋅THF) and borane dimethyl sulfide complex (BH 3 ⋅SMe 2 ). In addition, this methodology requires only a small excess of reducing agent and therefore compares favourably not just with other borane reductants that do not require a metal co‐catalyst, but also with silane and aluminium based reagents.