Copper-Mediated Introduction of the CF PO(OEt) Motif: Scope and Limitations.

Chemistry

Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.

Published: December 2017

AI Article Synopsis

  • A new method for creating CF PO(OEt) compounds is introduced, using the reagent CuCF PO(OEt) in a straightforward way that works with various types of substrates.
  • This procedure effectively transforms aryl diazonium salts and different iodonium salts into fluorinated compounds at room temperature.
  • The study also explores the reaction's mechanics and expands its application to other organic compounds, including vinyl/aryl iodides and disulfides, highlighting its potential and limitations.

Article Abstract

Herein, a general procedure to access CF PO(OEt) -containing molecules is reported. The reagent CuCF PO(OEt) 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 SCF PO(OEt) -containing molecules.

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http://dx.doi.org/10.1002/chem.201703542DOI Listing

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