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Stoichiometric and catalytic aryl-perfluoroalkyl coupling at tri-tert-butylphosphine palladium(II) complexes

Ferguson, DM, Bour, JR, Canty, AJ, Kampf, JW and Sanford, MS 2017 , 'Stoichiometric and catalytic aryl-perfluoroalkyl coupling at tri-tert-butylphosphine palladium(II) complexes' , Journal of the American Chemical Society, vol. 139, no. 34 , pp. 11662-11665 , doi: 10.1021/jacs.7b05216.

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Abstract

This Communication describes studies of Ph–RF (RF = CF3 or CF2CF3) coupling at Pd complexes of general structure (PtBu3)PdII(Ph)(RF). The CF3 analogue participates in fast Ph-CF3 coupling (α-fluoride elimination at the 3-coordinate PdII complex. Furthermore, they show that this undesired pathway can be circumvented by changing from a CF3 to a CF2CF3 ligand. Ultimately, the insights gained from stoichiometric studies enabled the identification of Pd(PtBu3)2 as a catalyst for the Pd-catalyzed cross-coupling of aryl bromides with TMSCF2CF3 to afford pentafluoroethylated arenes.

Item Type: Article
Authors/Creators:Ferguson, DM and Bour, JR and Canty, AJ and Kampf, JW and Sanford, MS
Keywords: catalysis, palladium, fluorocarbon, DFT
Journal or Publication Title: Journal of the American Chemical Society
Publisher: American Chemical Society
ISSN: 0002-7863
DOI / ID Number: 10.1021/jacs.7b05216
Copyright Information:

Copyright 2017 American Chemical Society

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