Abstract
The synthesis of arylCF2CF2SiMe3 and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-arylethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 °C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.
Highlights
The Ruppert-Prakash reagent (CF3TMS) is a stable and easy to handle commercially available reagent widely employed for late stage trifluoromethylation.[1]
These complexes were successfully used in cross-coupling reactions with aryl iodides; the use of gaseous TFE is not ideal for common research laboratory settings, and the sensitivity of the [CuOtBu]4 precursor may be limiting as a glove box is preferable for handling.[9]
Our research program on Cu-mediated 18F-radiochemistry for Positron Emission Tomography (PET) applications is currently expanding with the development of new methodologies for the labeling of perfluorinated arenes.[10]
Summary
The Ruppert-Prakash reagent (CF3TMS) is a stable and easy to handle commercially available reagent widely employed for late stage trifluoromethylation.[1]. The cooperative effect of silver in the Cu-catalyzed trifluoromethylation of aryl iodides with CF3TMS has been reported for other systems by Weng and co-workers.4e Alternative sources of Cu(I) such as CuBr or CuCl were less effective (Table 1, entries 7–8).[14] The reaction did proceed with a catalytic amount of CuI, a substantial amount of by-product formation was observed (entry 9).
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
