Copper‐Mediated [(Diethylphosphono)difluoromethyl]thiolation of α‐Bromo Ketones. Issue 17 (3rd May 2017)

• Record Type: Journal Article
• Authors: Ivanova, Maria V.; Bayle, Alexandre; Besset, Tatiana; Pannecoucke, Xavier; Poisson, Thomas
• Is Part Of: European journal of organic chemistry. Issue 17(2017)
• Page Start: 2475
• Page End: 2480
• Publication Date: 2017-05-03
• Subjects: Fluorine -- Copper -- Synthetic methods -- Sulfur; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700182
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : We report herein a straightforward access to α‐[(diethoxyphosphoryl)difluoromethyl]thiolated ketones. The methodology, which involves the nucleophilic [Cu]CF2 PO(OEt)2 species, has allowed the formation of the targeted compounds in moderate to high yields by using a simple procedure. This method represents a convenient alternative to the known approaches for the introduction of this emergent fluorinated motif. Abstract : The synthesis of α‐[(diethylphosphono)difluoromethyl]thiolated ketones starting from the corresponding α‐bromo ketones is reported. By using the nucleophilic [Cu]CF2 PO(OEt)2 species prepared from CuSCN, the thiolated ketones were obtained in moderate to high yields using a simple procedure.