Fluorobenzoic acid coformers to improve the solubility and permeability of the BCS class IV drug naftopidil DOI
M. K. Chaitanya Mannava, Manish Kumar Bommaka, Rambabu Dandela

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(37), P. 5582 - 5585

Published: Jan. 1, 2022

Crystalline salts of the low solubility and permeability drug naftopidil were investigated with mono-, di-, tri-, tetrafluorobenzoic acids as coformers to show that 245TFBA (2,4,5-trifluorobenzoic acid) is optimal salt faster dissolution high permeability, thereby opening study fluorinated in pharmaceutical cocrystals salts.

Language: Английский

Fluoroalkyl N-Triftosylhydrazones as Easily Decomposable Diazo Surrogates for Asymmetric [2 + 1] Cycloaddition: Synthesis of Chiral Fluoroalkyl Cyclopropenes and Cyclopropanes DOI
Xinyu Zhang,

Chunqi Tian,

Zhanjing Wang

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(14), P. 8527 - 8537

Published: June 29, 2021

The development of asymmetric carbene transfer reactions using N-sulfonylhydrazones as the diazo surrogate is a long-term issue in organic synthesis since commonly require high temperatures for their decomposition to release reactive compounds. We report on use fluoroalkyl-aryl ketone N-triftosylhydrazones class N-sulfonylhydrazone capable decomposing below 0 °C (to −40 °C). Their application [2 + 1] cycloadditions with alkynes and alkenes catalyzed by chiral rhodium catalyst described. This protocol affords wide variety fluoroalkylated cyclopropenes cyclopropanes yields enantioselectivity demonstrates broad functional group tolerance. It noteworthy that these small-ring products feature fluoroalkyl quaternary carbon center. origin cyclopropenation reaction was rationalized density theory calculations.

Language: Английский

Citations

43
Recent advances in pyrazole synthesis employing diazo compounds and synthetic analogues DOI

Sanoop P. Chandrasekharan,

Anamika Dhami, Sandeep Kumar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(45), P. 8787 - 8817

Published: Jan. 1, 2022

This review summarizes the recent developments in construction of pyrazoles using diazo compounds, nitrile imines and their synthetic equivalents.

Language: Английский

Citations

38
Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides DOI
Wei Wu,

Yi You,

Zhiqiang Weng

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 33(10), P. 4517 - 4530

Published: Jan. 21, 2022

Language: Английский

Citations

29
Design, synthesis, and molecular docking of novel pyrazole-chalcone analogs of lonazolac as 5-LOX, iNOS and tubulin polymerization inhibitors with potential anticancer and anti-inflammatory activities DOI

Asmaa Ahmed,

Mamdouh F. A. Mohamed, Rasha M. Allam

et al.

Bioorganic Chemistry, Journal Year: 2022, Volume and Issue: 129, P. 106171 - 106171

Published: Sept. 22, 2022

Language: Английский

Citations

29
Merging Copper(I) Photoredox Catalysis and Iodine(III) Chemistry for the Oxy‐monofluoromethylation of Alkenes DOI
Nagarajan Ramkumar,

Л. Баумане,

Dzintars Začs

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(12)

Published: Jan. 24, 2023

A simple process for the oxy-monofluoromethylation of alkenes is described. In combination with visible-light copper(I) photoredox catalysis, an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands serves as a powerful source monofluoromethyl (CH2 F) radical, enabling step economical synthesis γ-fluoro-acetates from broad range olefinic substrates under mild conditions. Applications to late-stage diversification derived complex molecules, amino acids and fluoromethylated heterocycles are also demonstrated.

Language: Английский

Citations

17
Visible‐Light Photoredox‐Catalyzed Radical Fluoromethoxylation of Olefins DOI
Nagarajan Ramkumar,

Arturs Sperga,

Sergey Belyakov

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1405 - 1412

Published: April 7, 2023

Abstract Fluoroalkyl ethers have attracted considerable research interest in the fields of pharmaceutical, agrochemical, nuclear imaging and material sciences, forging development new synthetic methods to access this class compounds. Radical fluoroalkoxylation has recently emerged as a promising approach for synthesizing fluoroalkyl ethers. Herein, solid, easy‐to‐access redox‐active N−O reagent, 1‐(fluoromethoxy)‐3‐methyl‐benzotriazolium triflate (FMBT), serving radical source (mono)fluoromethoxy group under photocatalytic conditions, was introduced. The potential FMBT demonstrated functionalization olefins amino keto‐monofluoromethyl ethers, benefiting related study context chemical biology drug discovery. magnified image

Language: Английский

Citations

17
Photocatalytic Boryl Radicals Triggered Sequential B─N/C─N Bond Formation to Assemble Boron‐Handled Pyrazoles DOI Creative Commons
Yang Xie, Ruilong Zhang,

Ze‐Le Chen

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 11(3)

Published: Nov. 29, 2023

Abstract Vinyldiazo compounds are one of the most important synthons in construction a cyclic ring. Most photochemical transformations vinyldiazo mainly focusing on utilization their C═C bond site, while reactions taking place at terminal nitrogen atom largely unexplored. Herein, photocatalytic cascade radical cyclization LBRs with reagents through sequential B─N/C─N formation is described. The reaction starts addition (Lewis base–boryl radicals) diazo followed by intramolecular to access wide range boron‐handled pyrazoles good excellent yields. Control experiments, together detailed mechanism studies well explain observed reactivity. Further demonstrate utility this approach for applications pharmaceutical and agrochemical research.

Language: Английский

Citations

17
Photoredox Catalyzed Radical Fluoroalkylation with Non-Classical Fluorinated Reagents DOI

Yao Ouyang,

Feng‐Ling Qing

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 2815 - 2824

Published: Feb. 22, 2024

The emergence of photocatalysis has greatly advanced radical fluoroalkylation reactions. Central to this advancement is the introduction and refinement reagents, which play a pivotal role in driving these reactions forward. Intriguingly, some previously not recognized for their properties, have emerged as key players area. In Perspective, we provide an overview four representative reagents pioneered by our laboratory, subsequently garnered extensive application broader research contexts, including difluorocarbene precursors bromodifluoromethylphosphonium bromide, electrophilic sulfonylation reagent triflic anhydride, nucleophilic trifluoromethylation methyl fluorosulfonyldifluoroacetate (Chen's reagent). integration phosphonium into enabled unexpected reactivities now notably expanded capabilities difluoromethylation, trifluoromethylation, difluoroalkylation. Our discussion highlights how atypical enriched toolkit available fluoroalkylations, offering insights that could inspire future

Language: Английский

Citations

6
High‐Valent Copper Catalysis Enables Regioselective Fluoroarylation of Gem‐Difluorinated Cyclopropanes DOI Creative Commons
Xiuli Wu,

Xiangyu Song,

Ying Xia

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(18)

Published: March 9, 2024

Abstract Transition‐metal (TM) catalyzed reaction of gem ‐difluorinated cyclopropanes ( ‐DFCPs) has drawn much attention recently. The generally occurs via the activation distal C─C bond in ‐DFCPs by a low‐valent TM through oxidative addition, eventually producing mono‐fluoro olefins as coupling products. However, achieving regioselective proximal that overcomes intrinsic reactivity catalysis remains elusive. Here, new mode enabled high‐valent copper catalysis, which allows exclusive congested is presented. achieves fluoroarylation uses NFSI (N‐fluorobenzenesulfonimide) electrophilic fluoro reagent and arenes C─H nucleophiles, enabling synthesis diverse CF 3 ‐containing scaffolds. It proposed species plays an important role possibly σ‐bond metathesis.

Language: Английский

Citations

6
Fluoroalkyl N-sulfonyl hydrazones: An efficient reagent for the synthesis of fluoroalkylated compounds DOI
Paramasivam Sivaguru, Xihe Bi

Science China Chemistry, Journal Year: 2021, Volume and Issue: 64(10), P. 1614 - 1629

Published: Aug. 31, 2021

Language: Английский

Citations

35