Convenient synthesis of perfluoroalkyltrifluoroborates

Sprenger, Jan A. P.; Kerpen, Christoph; Ignat’ev, Nikolai; Finze, Maik

doi:10.1016/j.jfluchem.2017.12.004

Cited by 11 publications

(5 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Perfluoroalkylcyanoborates having longer perfluoroalkyl chains were prepared from perfluoroalkyltrifluoroborates M [ R F BF 3 ] ( M = K, Na) and (CH 3 ) 3 SiCN (Scheme ) ,…”

Section: Perfluoroalkyl‐ Alkyl‐ and Alkoxycyanoboratesmentioning

confidence: 99%

“…However, the syntheses described for their salts in the earlier literature were not convenient for practical applications because of the need of toxic and moisture sensitive chemicals, like gaseous BF 3 , concentrated hydrofluoric acid, or anhydrous HF. Simple and inexpensive methods for the preparation of perfluoroalkyltrifluoroborates K[ R F BF 3 ] ( R F = CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9 ) starting from commercially available chemicals have been published by us, recently . Reactions of perfluoroalkyltrifluoroborates K[ R F BF 3 ] ( R F = CF 3 , C 2 F 5 , n C 3 F 7 , n C 4 F 9 ) with trimethylsilyl cyanide proceeded stepwise.…”

Section: Perfluoroalkyl‐ Alkyl‐ and Alkoxycyanoboratesmentioning

confidence: 99%

“…The lower stability of CF 3 ‐borates in comparison to C 2 F 5 ‐borates is a common feature that was explained by the easy loss of F – followed by elimination of difluorocarbene in case of CF 3 –B compounds. [7a], [7b], [7c], [117a], …”

Section: Perfluoroalkyl‐ Alkyl‐ and Alkoxycyanoboratesmentioning

confidence: 99%

See 2 more Smart Citations

Cyanoborates

Ignat’ev

Finze

2019

Eur J Inorg Chem

Self Cite

View full text Add to dashboard Cite

Cyanoborate chemistry has emerged to an important topic during the last two decades, beginning with two independent reports on the successful synthesis of the tetracyanoborate anion [B(CN) 4 ]in 2000. A wealth of cyanoborate anions with different substituents in addition to CN group(s) bonded to boron, i.e. hydrogen, halogen, aryl, alkenyl, alkyl, perfluoroalkyl, and alkoxy, have been developed, which enable the tuning of properties of compounds and materials based on them. The readily accessible alkali metal cyanoborates are convenient starting materials for the preparation of cyanoborates with various organic, inorganic, and metal cations as well as cyanoborate coordination compounds. A focus has been on low-[a] Julius-Maximilians-Universität Würzburg,

show abstract

“…Perfluoroalkylcyanoborates having longer perfluoroalkyl chains were prepared from perfluoroalkyltrifluoroborates M [ R F BF 3 ] ( M = K, Na) and (CH 3 ) 3 SiCN (Scheme ) ,…”

Section: Perfluoroalkyl‐ Alkyl‐ and Alkoxycyanoboratesmentioning

confidence: 99%

Section: Perfluoroalkyl‐ Alkyl‐ and Alkoxycyanoboratesmentioning

confidence: 99%

See 1 more Smart Citation

Cyanoborates

Ignat’ev

Finze

2019

Eur J Inorg Chem

Self Cite

View full text Add to dashboard Cite

show abstract

“… [25] Ionic liquids with these anions [ R F BF 3− x (CN) x ] − ( x =1−3; R F =C n F 2 n +1 , n =1−4) possess low dynamic viscosities, high specific conductivities, and remarkable electrochemical stabilities. These ILs have been conveniently prepared from readily accessible salts of perfluoroalkyltrifluoroborate anions [ R F BF 3 ] − [43] . However, the costs for the introduction of perfluoroalkyl groups at boron are relatively high and depend on the price of the starting reagents C n F 2 n +1 I or C n F 2 n +1 H.…”

Section: Introductionmentioning

confidence: 99%

“…These ILs have been conveniently prepared from readily accessible salts of perfluoroalkyltrifluoroborate anions [R F BF 3 ] À . [43] However, the costs for the introduction of perfluoroalkyl groups at boron are relatively high and depend on the price of the starting reagents…”

Section: Introductionmentioning

confidence: 99%

Alkylcyanoborate Anions: Building Blocks for Fluorine‐Free Low‐Viscosity, Electrochemically and Thermally Stable Ionic Liquids

Schopper

Landmann

Sprenger

et al. 2023

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

A set of mixed‐substituted potassium alkylcyano‐ and alkylcyanofluoroborates has been synthesized using easily accessible starting compounds and characterized by elemental analysis, NMR and vibrational spectroscopy, and mass spectrometry. In addition, single‐crystal structures of salts of the cyanoborate anions have been derived from X‐ray diffraction experiments. The 1‐ethyl‐3‐methylimidazolium room temperature ionic liquids ([EMIm]+‐RTILs) with the new borate anions have been synthesized and their physicochemical properties, that is, high thermal and electrochemical stability, low viscosity, and high conductivity, have been compared to the properties of related [EMIm]+‐RTILs. The influence of the different alkyl substituents at boron has been assessed. The exemplary study on the properties with the [EMIm]+‐ILs with the mixed water stable alkylcyanoborate anions points towards the potential of these fluorine‐free borate anions, in general.

show abstract

Convenient Preparation and Structure Determination of Air‐ and Moisture‐Tolerant Difluoromethylborates

Yokawa

Ito

2020

Chemistry An Asian Journal

View full text Add to dashboard Cite

Convenient and reliable synthetic methods for difluoromethylborates have been established. The intermediary generated difluoromethylsilicate species from TMSCF 2 H (TMS = trimethylsilyl) and potassium tert-butoxide were allowed to react with pinBPh (Me 4 C 2 O 2 BPh) in the presence of 18-crown-6 to give the corresponding borate compound [pinB(Ph)CF 2 H] À K + (18-crown-6) as an air-and moisture-tolerant solid. The unambiguously determined crystal structure of [pinB(Ph)CF 2 H] À K + (18-crown-6) revealed that the difluoromethylborate unit partially coordinated on the potassium ion. Reaction of [pinB(Ph)CF 2 H]-K + (18-crown-6) with potassium difluoride (KHF 2) in acetic acid enabled substitution of the pinacol unit and phenyl group with fluorides, and gave (difluoromethyl)trifluoroborate [F 3 BCF 2 H]-K + (18-crown-6) in a good yield. The crystal structure of air-and moisturetolerant [F 3 BCF 2 H]-K + (18-crown-6), which would be a promising reagent for synthesis of various difluoromethylboron species, showed a polyrotaxane-like polymeric structure based on the K•••F interactions between the K + (18-crown-6), CF 2 H, and BF 3 units.

show abstract

Convenient synthesis of perfluoroalkyltrifluoroborates

Cited by 11 publications

References 59 publications

Cyanoborates

Cyanoborates

Alkylcyanoborate Anions: Building Blocks for Fluorine‐Free Low‐Viscosity, Electrochemically and Thermally Stable Ionic Liquids

Convenient Preparation and Structure Determination of Air‐ and Moisture‐Tolerant Difluoromethylborates

Contact Info

Product

Resources

About