Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E

Gonay, Marie; Batisse, Chloé; Paquin, Jean‐François

doi:10.1021/acs.joc.0c01377

Cited by 36 publications

(26 citation statements)

References 40 publications

(72 reference statements)

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“…These fluorochemicals are hydrolysis products of LiPF 6 with H 2 O. [12e] Besides, a new peak appeared at 16.8 ppm in BA-added electrolyte corresponds to R-COF, [17] produced by the reaction of BA with HF. These outcomes confirm that additive BA can scavenge HF completely and effectively inhibit the decomposition of LiPF 6 .…”

Section: Resultsmentioning

confidence: 99%

Benzoic Anhydride as a Bifunctional Electrolyte Additive for Hydrogen Fluoride Capture and Robust Film Construction over High‐Voltage Li‐Ion Batteries

Jiang

Yin

et al. 2021

ChemSusChem

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High-voltage LiNi 0.8 Co 0.1 Mn 0.1 O 2 (NCM811)-based Li-ion batteries (LIBs) with enhanced performance can be achieved by properly tailoring the electrolyte systems. Benzoic anhydride (BA) was proposed here as a promising bifunctional electrolyte additive that can not only construct a robust cathode-electrolyte interface (CEI) film on the electrode surface but also capture HF/H 2 O in the electrolyte effectively. Compared to the cell without the BA additive, the capacity of Li/NCM811 half-cell with 1.0 wt % BA was increased from 128.5 to 149.6 mAh g À 1 after 200 cycles at 1 C between 3.0 and 4.3 V. Even at a higher cut-off voltage of 4.5 V, the BA-containing Li/NCM811 half-cell delivered a capacity retention of 69 % after 200 cycles, much higher than that of the half-cell without the additive (56 %). Both theoretical calculation and experimental results verified that the BA additive could be preferentially oxidized to form a stable interface film with high conductivity that protected the NCM811 cathode and suppressed the decomposition of the electrolyte.

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Section: Resultsmentioning

confidence: 99%

Benzoic Anhydride as a Bifunctional Electrolyte Additive for Hydrogen Fluoride Capture and Robust Film Construction over High‐Voltage Li‐Ion Batteries

Jiang

Yin

et al. 2021

ChemSusChem

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“…Moderate to excellent yields were obtained by using catalytic quantities of sodium fluoride starting with both aliphatic and aromatic carboxylic acids (Scheme 11a). 28 Although acyl fluorides can be purified simply by filtration over silica gel, it has also been demonstrated that a sequential amidation could be achieved directly without purification of the intermediate acyl fluorides (Scheme 11b).…”

Section: Short Review Synthesismentioning

confidence: 99%

Recent Advances in the Synthesis of Acyl Fluorides

Gonay¹,

Batisse²,

Paquin³

2020

Synthesis

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Acyl fluorides are valuable intermediates in organic synthesis. They are increasingly employed in peptide synthesis, in challenging esterification and amidation reactions or in transition-metal-catalyzed transformations. This review summarizes recent advances in their preparation.1 Introduction2 Nucleophilic Fluorination2.1 α-Fluoroamine Reagents2.2 Sulfur-Based Reagents2.3 Metal Catalysts2.4 Phosphorus-Based Reagents2.5 N,N′-Dicyclohexylcarbodiimide/HF·Pyridine2.6 Uranium Hexafluoride2.7 Bromine Trifluoride3 Radical Fluorination4 Conclusion

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“…In addition to our direct cross-coupling reaction method, several useful synthetic methods for the formation of acyl fluorides have become available in recent years [19][20][21][22][23]. In this context, we were interested in the functional transformation of an acyl fluoride unit into a CF 3 motif.…”

Section: Introductionmentioning

confidence: 99%

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD^®/Olah’s reagent under solvent-free conditions

Liang

Taya

Zhao

et al. 2020

Beilstein J. Org. Chem.

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A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD® and Olah’s reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.

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Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E

Cited by 36 publications

References 40 publications

Benzoic Anhydride as a Bifunctional Electrolyte Additive for Hydrogen Fluoride Capture and Robust Film Construction over High‐Voltage Li‐Ion Batteries

Benzoic Anhydride as a Bifunctional Electrolyte Additive for Hydrogen Fluoride Capture and Robust Film Construction over High‐Voltage Li‐Ion Batteries

Recent Advances in the Synthesis of Acyl Fluorides

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD^®/Olah’s reagent under solvent-free conditions

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Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E

Cited by 36 publications

References 40 publications

Benzoic Anhydride as a Bifunctional Electrolyte Additive for Hydrogen Fluoride Capture and Robust Film Construction over High‐Voltage Li‐Ion Batteries

Benzoic Anhydride as a Bifunctional Electrolyte Additive for Hydrogen Fluoride Capture and Robust Film Construction over High‐Voltage Li‐Ion Batteries

Recent Advances in the Synthesis of Acyl Fluorides

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions

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Product

Resources

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Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD^®/Olah’s reagent under solvent-free conditions