Zhou Q, Ruffoni A, Gianatassio R, Fujiwara Y, Sella E, Shabat D, Baran PS * The Scripps Research Institute, La Jolla, USA and Tel-Aviv University, Israel
Direct Synthesis of Fluorinated Heteroarylether Bioisosteres.
Angew. Chem. Int. Ed. 2013;
52: 3949-3952
Key words
difluoroethylation - bioisosteres - C–H functionalization
Significance
A novel protocol for direct difluoroethylation of a broad range of heterocycles, Michael acceptors and even thiols with sodium difluoroethylsulfinate (DFES-Na) has been described. DFES-Na is shown to be compatible with various sensitive functional groups, reacts site selectively in high conversion and is easy to handle.
Comment
Interestingly, performing the reaction with DFES-Na and tert-butylhydroperoxide (TBHP) solely results in only traces of the desired product. Only after addition of stoichiometric amounts of ZnCl2 and TsOH·H2O, the product is obtained in high yield.
