2009
DOI: 10.1002/ange.200805041
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CF Activation at Rhodium Boryl Complexes: Formation of 2‐Fluoroalkyl‐1,3,2‐Dioxaborolanes by Catalytic Functionalization of Hexafluoropropene

Abstract: Fluorierte Bausteine durch C‐F‐Bindungsspaltung: Die Synthese neuartiger Dioxaborolane durch katalytische C‐F‐Aktivierung wird vorgestellt (siehe Schema). Die Reaktionen verlaufen bei Raumtemperatur, wobei als katalytische Zwischenstufen vermutlich Rhodiumhydrid‐ und Borylspezies auftreten.

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Cited by 69 publications
(39 citation statements)
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“…[15] Variable-temperature 31 P NMR analysis shows that the free phosphine has no influence on the dynamic behavior, which suggests that the process is intramolecular. [8] A signal at d = À10.18 ppm in the 1 H NMR spectrum of 6 confirms the presence of the hydrido ligand. The resonance features characteristic couplings for a rhodium(I) compound, with doublet couplings to rhodium and to phosphorus of 166 Hz and 30 Hz, respectively.…”
mentioning
confidence: 73%
See 1 more Smart Citation
“…[15] Variable-temperature 31 P NMR analysis shows that the free phosphine has no influence on the dynamic behavior, which suggests that the process is intramolecular. [8] A signal at d = À10.18 ppm in the 1 H NMR spectrum of 6 confirms the presence of the hydrido ligand. The resonance features characteristic couplings for a rhodium(I) compound, with doublet couplings to rhodium and to phosphorus of 166 Hz and 30 Hz, respectively.…”
mentioning
confidence: 73%
“…[8] Rhodium(I)-boryl complexes are almost without any precedent in the literature, [1,9] although [Rh(Bcat)(PMe 3 ) 4 ] has been synthesized by Marder and co-workers from the treatment of [Rh(Me)-(PMe 3 ) 4 ] with B 2 cat 2 (Bcat = B{1,2-O 2 C 6 H 4 }). The thermodynamic driving force in this case is apparently the generation of B À F bonds.…”
mentioning
confidence: 99%
“…[34] Verwendet man dagegen das Boran HBpin (HBpin = 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan), wird Hexafluorpropen katalytisch zu einer Mischung von Fluoralkyl-Dioxaborolanen umgesetzt (TON bis zu 250, TOF 12.5 h À1 ). [35] Die intermediäre Bildung einer Rh I -Boryl-Verbindung kann auf Grundlage einer unabhän-gigen Synthese des Komplexes 59 vermutet werden, der Hexafluorpropen sowohl in 2-als auch in 3-Stellung zu aktivieren vermag. [30] Eine vçllig andere Strategie zur HDF von Olefinen wurde von der Gruppe um Ishihara verfolgt.…”
Section: Schema 12unclassified
“…[5,6] The few examples of catalytic activation of fluoroalkenes have a common drawback, as they are either costly or slow and inefficient in terms of turnover frequencies (TOFs) and turnover numbers (TONs), not to mention that the high sensitivity of most catalysts limits possible practical applications. [7] Complexes of the less expensive Group 4 metals are reactive towards fluoroalkenes, as shown by Jones et al in stoichiometric hydrodefluorination (HDF) employing zirconium and hafnium hydrides. [8] However, C-F activation catalyzed by Group 4 metals is known only for fluoroarenes.…”
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confidence: 95%