Organic Chemistry: Current Research
Open Access

Copper-mediated synthesis of (diethylphosphono)difluoromethyl thioethers from diazonium salts, NaSCN, and TMS-CF₂PO(OEt)₂

10^th European Organic Chemistry Congress

March 21-22, 2019 | Rome, Italy

Yang Ou

Ruhr-University Bochum, Germany

Posters & Accepted Abstracts: Organic Chem Curr Res

Abstract :

Fluoroalkylthio groups are currently at the focus of interest due to their better biodegradability and enhanced lipophilicity in comparison to their fluoroalkylated counterparts. Whereas methodology to synthesize SCF3- and SCF2H-substituted compounds is already well developed, the introduction of functionalized fluoroalkylthio groups SCF2FG (FG = functional group) into functionalized molecules still poses substantial challenges. In this context, several functionalized electrophilic difluoromethylthio reagents have been used to access SCF2FG-containing molecules via electrophilic difluoromethylthiolations. Since these reagents are mostly generated from the corresponding nucleophilic TMS-CF2FG reagents via multi-step reactions, we reasoned that it would be more efficient to develop reaction sequences in which functionalized TMS-CF2 reagents could be used directly. We now disclose a synthesis of aromatic SCF2PO(OEt)2 compounds in which the sulfur originates from a simple thiocyanate salt, and the fluoroalkyl group from TMS-CF2PO(OEt)2. The key advantages of this protocol are its mild conditions, operational simplicity and broad substrate scope. Its preparative utility is demonstrated by the moderate-to-high-yielding synthesis of 22 (diethylphosphono)difluoromethyl thioethers bearing various functionalities.

Biography :

Yang Ou studied medicinal chemistry at the Peking University, acquiring his Master's degree in 2015. He is currently working towards his PhD at Ruhr-University Bochum under the supervision of Prof. Lukas J. Goossen. His research program is focused on the development of new strategies to access fluorinated molecules and heterocycles.