Copper‐Mediated Introduction of the CF2PO(OEt)2 Motif: Scope and Limitations

Herein, a general procedure to access CF2PO(OEt)2‐containing molecules is reported. The reagent CuCF2PO(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...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-12, Vol.23 (68), p.17318-17338
Main Authors: Ivanova, Maria V., Bayle, Alexandre, Besset, Tatiana, Pannecoucke, Xavier, Poisson, Thomas
Format: Article
Language:English
Subjects:
Chemical Sciences
copper
fluorine
phosphate mimic
synthetic methods
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Summary:Herein, a general procedure to access CF2PO(OEt)2‐containing molecules is reported. The reagent CuCF2PO(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 SCF2PO(OEt)2‐containing molecules. Upgrading reagents: A straightforward procedure to prepare the CuCF2PO(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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201703542