The Influence of the Nature of Phosphine Ligand on Palladium Catalysts for Cross-Coupling of Weakly Nucleophilic Potassium Pentafluorophenyltrifluoroborate with ArHal and PhCH2Hal (Hal=Br, Cl) Full article
| Journal |
Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416 |
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| Output data | Year: 2014, Volume: 70, Number: 23, Pages: 3720-3725 Pages count : 6 DOI: 10.1016/j.tet.2014.04.019 | ||||
| Tags | Aryl halides, Bulky phosphine, Cross-coupling, Palladium catalyst, Polyfluorinated organotrifluoroborates | ||||
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| Affiliations |
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Funding (1)
| 1 | Federal Agency for Scientific Organizations | V.44.2.12. |
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.
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 PhCH2Hal (Hal=Br, Cl)
Tetrahedron. 2014. V.70. N23. P.3720-3725. DOI: 10.1016/j.tet.2014.04.019 WOS Scopus РИНЦ ANCAN OpenAlex
The Influence of the Nature of Phosphine Ligand on Palladium Catalysts for Cross-Coupling of Weakly Nucleophilic Potassium Pentafluorophenyltrifluoroborate with ArHal and PhCH2Hal (Hal=Br, Cl)
Tetrahedron. 2014. V.70. N23. P.3720-3725. DOI: 10.1016/j.tet.2014.04.019 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Nov 12, 2013 |
| Accepted: | Apr 7, 2014 |
| Published online: | Apr 13, 2014 |
| Published print: | Jun 10, 2014 |
Identifiers:
| Web of science: | WOS:000336191600011 |
| Scopus: | 2-s2.0-84899965937 |
| Elibrary: | 21877201 |
| Chemical Abstracts: | 2014:672473 |
| Chemical Abstracts (print): | 160:691051 |
| OpenAlex: | W2950267769 |