Journal
TETRAHEDRON
Volume 70, Issue 23, Pages 3720-3725Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.04.019
Keywords
Cross-coupling; Palladium catalyst; Bulky phosphine; Polyfluorinated organotrifluoroborates; Aryl halides
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Funding
- Siberian Branch of the Russian Academy of Sciences (SB RAS) [V.44.2.12]
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The influence of the ligand nature on catalytic activity of palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate, which imitates the behavior of electron-deficient organoboron reagents, with aryl halides, ArHal (Hal=Br, Cl) was studied. The activity of the catalysts generated in situ from Pd(OAc)(2) and appropriate phosphorous containing ligands and the reaction selectivity was found to depend on the nature of bulky phosphines used as ligands. As a result, conditions for involving the electron-deficient organoboron reagent-potassium pentafluorophenyltrifluoroborate in the palladium-catalyzed cross-coupling with aryl bromides and aryl chlorides were identified. It was demonstrated that the chosen conditions are appropriate for the reaction of K[C6F5BF3] with benzyl chloride and benzyl bromide deriving pentafluorophenylarylmethanes, C6F5CH2Ar. (C) 2014 Elsevier Ltd. All rights reserved.
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