373-84-2Relevant articles and documents
Deoxygenative Fluorination of Phosphine Oxides: A General Route to Fluorinated Organophosphorus(V) Compounds and Beyond
Bornemann, Dustin,Brüning, Fabian,Grützmacher, Hansj?rg,Guan, Liangyu,Küng, Sebastian,Pitts, Cody Ross,Togni, Antonio,Trapp, Nils,Wettstein, Lionel
supporting information, p. 22790 - 22795 (2020/10/06)
Fluorinated organophosphorus(V) compounds are a very versatile class of compounds, but the synthetic methods available to make them bear the disadvantages of 1) occasional handling of toxic or pyrophoric PIII starting materials and 2) a dependence on hazardous fluorinating reagents such as XeF2. Herein, we present a simple solution and introduce a deoxygenative fluorination (DOF) approach that utilizes easy-to-handle phosphine oxides as starting materials and effectively replaces harsh fluorinating reagents by a combination of oxalyl chloride and potassium fluoride. The reaction has proven to be general, as R3PF2, R2PF3, and RPF4 compounds (as well as various cations and anions derived from these) are accessible in good yields and on up to a multi-gram scale. DFT calculations were used to bolster our observations. Notably, the discovery of this new method led to a convenient synthesis of 1) new difluorophosphonium ions, 2) hexafluorophosphate salts, and 3) fluorinated antimony- and arsenic- compounds.
Synthesis and Properties of Triarylhalostibonium Cations
Yang, Mengxi,Gabba?, Fran?ois P.
supporting information, p. 8644 - 8650 (2017/08/14)
As part of our fundamental interest in the chemistry of main-group Lewis acids, we have decided to target stibonium cations whose Lewis acidity is enhanced by the presence of a halogen substituent directly bound to antimony. Starting from Ph3Sb
Pd-catalyzed C-arylation of unsaturated compounds with pentavalent triarylantimony dicarboxylates
Moiseev, Dmitry V.,Gushchin, Aleksey V.,Shavirin, Andrey S.,Kursky, Yury A.,Dodonov, Viktor A.
, p. 176 - 184 (2007/10/03)
Triarylantimony (V) derivatives Ar3SbX2 (X = Hal or acyloxy) were prepared by reaction of Ar3Sb with equimolar amounts of a peroxide ROOH (R = t-Bu, H) in the presence of an acid or an anhydride in good to excellent yields. Ar3Sb(O2CR)2 are mild and efficient C-arylation reagents of unsaturated compounds (methyl acrylate, styrene, 2-phenylpropene and acrylonitrile) under palladium catalysis at 50 °C, with PdCl2 being the most effective catalyst. Ar3SbHal2 do not react under these conditions.
