Direct Superacid‐Promoted Difluoroethylation of Aromatics

Artault, Maxime; Vitse, Kassandra; Martin‐Mingot, Agnès; Thibaudeau, Sébastien

doi:10.1002/chem.202103926

Cited by 5 publications

(3 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, we assume that the strongest bond in organic chemistry [1] is further strengthened due to the protonation of the acyl fluoride moiety, based on the resonance stabilization of the carbon–fluorine bond. This is especially reinforced for analogous diprotonated superelectrophiles [37] …”

Section: Resultsmentioning

confidence: 91%

See 1 more Smart Citation

Strengthening of the C−F Bond in Fumaryl Fluoride with Superacids

Bayer

Kremser

Jessen

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

The reaction of fumaryl fluoride with the superacidic solutions XF/MF5 (X=H, D; M=As, Sb) results in the formation of the monoprotonated and diprotonated species, dependent on the stoichiometric ratio of the Lewis acid to fumaryl fluoride. The salts [C4H3F2O2]+[MF6]− (M=As, Sb) and [C4H2X2F2O2]2+([MF6]−)2 (X=H, D; M=As, Sb) are the first examples with a protonated acyl fluoride moiety. They were characterized by low‐temperature vibrational spectroscopy. Low‐temperature NMR spectroscopy and single‐crystal X‐ray structure analyses were carried out for [C4H3F2O2]+[SbF6]− as well as for [C4H4F2O2]2+([MF6]−)2 (M=As, Sb). The experimental results are discussed together with quantum chemical calculations of the cations [C4H4F2O2 ⋅ 2 HF]2+ and [C4H3F2O2 ⋅ HF]+ at the B3LYP/aug‐cc‐pVTZ level of theory. In addition, electrostatic potential (ESP) maps combined with natural population analysis (NPA) charges were calculated in order to investigate the electron distribution and the charge‐related properties of the diprotonated species. The C−F bond lengths in the protonated dication are considerably reduced on account of the +R effect.

show abstract

Section: Resultsmentioning

confidence: 91%

“…This Chemistry-A European Journal is especially reinforced for analogous diprotonated superelectrophiles. [37]…”

Section: Chemistry-a European Journalmentioning

confidence: 99%

Strengthening of the C−F Bond in Fumaryl Fluoride with Superacids

Bayer

Kremser

Jessen

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Currently, 30 is in phase I/Ib trial to evaluate its efficacy in advanced or metastatic ERα+ breast cancer ( Scott and Barlaam, 2022 ). Preliminary results show that 30 is well-tolerated and has a manageable safety profile ( Artault et al, 2022 ). However, poor metabolic stability and low ERα degradation activity in vivo have led to unsatisfactory results in phase I trials.…”

Section: Serdsmentioning

confidence: 99%

Optimization of small molecule degraders and antagonists for targeting estrogen receptor based on breast cancer: current status and future

Yao,

Tao,

et al. 2023

Front. Pharmacol.

View full text Add to dashboard Cite

The estrogen receptor (ER) is a classical receptor protein that plays a crucial role in mediating multiple signaling pathways in various target organs. It has been shown that ER-targeting therapies inhibit breast cancer cell proliferation, enhance neuronal protection, and promote osteoclast formation. Several drugs have been designed to specifically target ER in ER-positive (ER+) breast cancer, including selective estrogen receptor modulators (SERM) such as Tamoxifen. However, the emergence of drug resistance in ER+ breast cancer and the potential side effects on the endometrium which has high ER expression has posed significant challenges in clinical practice. Recently, novel ER-targeted drugs, namely, selective estrogen receptor degrader (SERD) and selective estrogen receptor covalent antagonist (SERCA) have shown promise in addressing these concerns. This paper provides a comprehensive review of the structural functions of ER and highlights recent advancements in SERD and SERCA-related small molecule drugs, especially focusing on their structural optimization strategies and future optimization directions. Additionally, the therapeutic potential and challenges of novel SERDs and SERCAs in breast cancer and other ER-related diseases have been discussed.

show abstract

Difluoroethylation Reactions of Organic Compounds

Tian,

Zheng,

Guo

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

Given the profound effect of fluorine‐containing groups in improving the chemical, physical, and biological properties of the parent compound, the fluorine‐containing groups were receiving increasing attention in the medicinal, pharmaceutical, agricultural, and material sciences. Unlike well‐developed trifluoromethylation and difluoromethylation reactions, the efficient and mild methods for rapid introduction of CF2Me are still underdeveloped, despite their important applications in pharmaceuticals and agrochemicals. This concept describes recent progress in difluoroethylation functionalization.

show abstract

Direct Superacid‐Promoted Difluoroethylation of Aromatics

Cited by 5 publications

References 47 publications

Strengthening of the C−F Bond in Fumaryl Fluoride with Superacids

Strengthening of the C−F Bond in Fumaryl Fluoride with Superacids

Optimization of small molecule degraders and antagonists for targeting estrogen receptor based on breast cancer: current status and future

Difluoroethylation Reactions of Organic Compounds

Contact Info

Product

Resources

About