Copper‐Mediated Introduction of the CF2PO(OEt)2 Motif: Scope and Limitations. Issue 68 (14th November 2017)

• Record Type: Journal Article
• Authors: Ivanova, Maria V.; Bayle, Alexandre; Besset, Tatiana; Pannecoucke, Xavier; Poisson, Thomas
• Is Part Of: Chemistry. Volume 23:Issue 68(2017)
• Page Start: 17318
• Page End: 17338
• Publication Date: 2017-11-14
• Subjects: copper -- fluorine -- phosphate mimic -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201703542
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Herein, a general procedure to access CF2 PO(OEt)2 ‐containing molecules is reported. The reagent CuCF2 PO(OEt)2 is accessible by a simple protocol and a broad range of substrates can be functionalised. The procedure allows the conversion of aryl diazonium salts, as well as aryl, heteroaryl, vinyl and alkynyl iodonium salts, into the corresponding fluorinated molecules at room temperature. Mechanistic studies were performed to gain a better understanding of the reaction pathway. Under similar conditions, vinyl and aryl iodides, allyl halides, and benzyl bromides were also functionalised, and the scope and limitations of the reaction were studied. Finally, the procedure was extended to disulfides to offer new access to SCF2 PO(OEt)2 ‐containing molecules. Abstract : Upgrading reagents : A straightforward procedure to prepare the CuCF2 PO(OEt)2 reagent from a readily available silylated precursor is reported. This reagent is used to functionalise aryl diazonium salts, aryl, heteroaryl, vinyl and alkynyl iodoniums salts (see scheme). The protocol was applied to the synthesis of bio‐relevant molecules.