Angewandte Chemie - International Edition p. 22790 - 22795 (2020)
Update date:2022-08-03
Topics: Phosphine Oxides Deoxygenative Fluorination Fluorinated Organophosphorus(V) Compounds
Bornemann, Dustin
Brüning, Fabian
Grützmacher, Hansj?rg
Guan, Liangyu
Küng, Sebastian
Pitts, Cody Ross
Togni, Antonio
Trapp, Nils
Wettstein, Lionel
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.
View MoreShandong Jiulong Hisince Pharmaceutical Co.,Ltd.
Contact:+86-15853188990
Address:Huadian Pioneer Park, Huadian Township, Qihe County, Dezhou City, Shandong, P.R.China
Jiangsu Chunjiang AgroChemical Co.,Ltd.
Contact:+86-13817348163
Address:Panjiawan 84, Zhixi Town, Jintan City, China
Wuxi Innopal International Trade CO.,LTD
Contact:+86-510-80711901-8003
Address:Room 402,Building 5,Longze Garden,No.17,South huanjiu Road,Yixing City, Jiangsu,China
HEZE KINGVOLT CHEMICAL CO., LTD
Contact:86-573-82118911
Address:Juancheng Industry Park
Shanghai Hohance Chemical Co., ltd
Contact:13914753421
Address:Fl.5;Bld. 70, Lane 1500; Xinfei Road
Doi:10.1021/ja0058381
(2001)Doi:10.1016/j.tet.2017.07.032
(2017)Doi:10.1039/c6ce02519f
(2017)Doi:10.1007/BF00567944
()Doi:10.1021/ja01156a111
(1951)Doi:10.1021/acs.joc.8b01956
(2018)