The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH(2)Hal (Hal=Br, Cl) Full article
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Tetrahedron
ISSN: 0040-4020 |
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| Output data | Year: 2014, Volume: 70, Number: 23, Pages: 3720-3725 Pages count : DOI: 10.1016/j.tet.2014.04.019 | ||||
| Tags | Cross-coupling; Palladium catalyst; Bulky phosphine; Polyfluorinated organotrifluoroborates; Aryl halides | ||||
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Abstract:
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.
Cite:
Shabalin A.Y.
, Adonin N.Y.
, Bardin V.V.
, Parmon V.N.
The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH(2)Hal (Hal=Br, Cl)
Tetrahedron. 2014. V.70. N23. P.3720-3725. DOI: 10.1016/j.tet.2014.04.019 WOS Scopus РИНЦ OpenAlex
The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH(2)Hal (Hal=Br, Cl)
Tetrahedron. 2014. V.70. N23. P.3720-3725. DOI: 10.1016/j.tet.2014.04.019 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Jun 1, 2014 |
Identifiers:
| Web of science: | WOS:000336191600011 |
| Scopus: | 2-s2.0-84899965937 |
| Elibrary: | 21877201 |
| OpenAlex: | W2950267769 |