5172-97-4Relevant articles and documents
Chalcogen OCF3 Isosteres Modulate Drug Properties without Introducing Inherent Liabilities
Ghiazza, Clément,Billard, Thierry,Dickson, Callum,Tlili, Anis,Gampe, Christian M.
supporting information, p. 1586 - 1589 (2019/08/26)
The synthesis of SCF3 as well as SeCF3 isosteres of two OCF3-containing drugs was achieved through visible light and copper-catalyzed processes. Herein, we show that chalcogen replacement modulates physicochemical and ADME properties without introducing intrinsic liabilities. The SCF3 and SeCF3 groups are more lipophilic than their oxygen counterpart; however, microsomal stability is unchanged, indicating that these molecular changes may be beneficial for in vivo half-life. Enabled by modern synthetic methods, we present the chalcogen-CF3 groups as potential key players for future fluorinated pharmaceuticals.
Highly Efficient C-SeCF3 Coupling of Aryl Iodides Enabled by an Air-Stable Dinuclear PdI Catalyst
Aufiero, Marialuisa,Sperger, Theresa,Tsang, Althea S.-K.,Schoenebeck, Franziska
supporting information, p. 10322 - 10326 (2015/09/01)
Building on our recent disclosure of catalysis at dinuclear PdI sites, we herein report the application of this concept to the realization of the first catalytic method to convert aryl iodides into the corresponding ArSeCF3 compounds. Highly efficient C-SeCF3 coupling of a range of aryl iodides was achieved, enabled by an air-, moisture-, and thermally stable dinuclear PdI catalyst. The novel SeCF3-bridged dinuclear PdI complex 3 was isolated, studied for its catalytic competence and shown to be recoverable. Experimental and computational data are presented in support of dinuclear PdI catalysis.
