HFIP in Organic Synthesis

Chemical Reviews, Год журнала: 2022, Номер 122(15), С. 12544 - 12747

Опубликована: Июль 17, 2022

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.

Язык: Английский

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Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023)

Organic Process Research & Development, Год журнала: 2024, Номер 28(2), С. 338 - 366

Опубликована: Янв. 18, 2024

This review summarizes examples of organic electrosynthesis from the peer-reviewed literature 2000 to 2023 that have been conducted on scales 20 g or above. A significant portion these were a ≤100 scale, while detailed reports kilogram-scale remain scarce in pharmaceutical industry. In addition chemical transformation, this also highlights type reactor used and projected productivity metric as ways compare different reports. The selected scale-ups described herein illustrate remaining challenges currently preventing routine use large-scale

Язык: Английский

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Hydrogen bonding-enabled gold catalysis: ligand effects in gold-catalyzed cycloisomerizations in hexafluoroisopropanol (HFIP)

Chemical Communications, Год журнала: 2022, Номер 58(61), С. 8516 - 8519

Опубликована: Янв. 1, 2022

Gold catalysis has witnessed immense evolution in recent years, yet it still requires the use of activators to render common [AuCl(L)] complexes catalytically active. Herein, H-bonding donor properties hexafluoroisopropanol (HFIP) are utilized for Au-Cl bond activation and ancillary ligand counteranion effects on cycloisomerization reactions showcased HFIP as solvent.

Язык: Английский

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Amplifying Hole Extraction Characteristics of PEDOT:PSS via Post-treatment with Aromatic Diammonium Acetates for Tin Perovskite Solar Cells

ACS Energy Letters, Год журнала: 2023, Номер 8(8), С. 3280 - 3287

Опубликована: Июль 11, 2023

We modify the PEDOT:PSS hole transport layer (HTL), commonly adopted for high-performance tin perovskite solar cells (TPSCs), via post-treatment of its surface using aromatic diammonium acetate salts dissolved in a highly volatile but interactive solvent. The solvent partly etches excessive insulating PSS while enabling tight anchoring to HTL. improve not only PEDOT:PSS/perovskite interface also top thin films, leading reduced defects, larger built-in potentials, and suppressed pinhole defects. In addition, transform PEDOT structure from benzoid quinoid depopulate charge carriers promote extraction. Consequently, TPSCs attain high efficiency 12.1% under standard 1 sun light illumination impressive stability without encapsulation ∼2800 h an N2 atmosphere. developed straightforward impactful method broader applications.

Язык: Английский

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Empirical Hydrogen Bonding Donor (HBD) Parameters of Organic Solvents Using Solvatochromic Probes – A Critical Evaluation

ChemPhysChem, Год журнала: 2023, Номер 24(9)

Опубликована: Янв. 18, 2023

Abstract The solvatochromicity of established solvatochromic UV/Vis probes, which appear to be sensitive the so‐called hydrogen bond donor (HBD) property solvent, is analysed using hydroxyl group density alcoholic solvents D HBD as a physical parameter in comparison pKa, chemical benchmark for acidity. Reichardt's dye B30 , Kosowers Z ‐indicator 1‐ethyl‐4‐(methoxycarbonyl) pyridinium iodide ( K ), Kamlet‐Tafts α, Dragos S parameter, Catalans SA scale, cis ‐dicyano‐bis (1,10‐phenanthroline) iron II complex (Schilt's Ferrocyphen dye, Fe ) and Gutmann‘s acceptor number AN have been investigated. observed dependencies empirical polarity parameters function several solvent families requires ompletely new physicochemical understanding these parameters. Only scale (or able bridge gap between global acidity, provided values are interpreted correctly applied accordingly.

Язык: Английский

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Optimizing solvent systems for electrospun PLGA scaffolds: effects on microstructure and mechanical properties for biomedical applications

RSC Advances, Год журнала: 2025, Номер 15(5), С. 3259 - 3272

Опубликована: Янв. 1, 2025

Optimizing solvent systems for electrospun PLGA tissue scaffolds enables control over mechanical properties. Hansen solubility theory helps identify key effects, enabling the design of tunable, high-performance biomedical use.

Язык: Английский

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Electrochemical oxidative thiocyanation and amination of enaminones towards the synthesis of multi-substituted alkenes

Green Chemistry, Год журнала: 2020, Номер 23(2), С. 763 - 766

Опубликована: Дек. 11, 2020

A highly stereoselective synthesis of thiocyanated enaminones was achieved by an electrochemical process, which involved C–H bond thiocyanation and vinyl C–N transamination.

Язык: Английский

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Regio- and stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

Green Chemistry, Год журнала: 2021, Номер 23(6), С. 2420 - 2426

Опубликована: Янв. 1, 2021

An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction sulfonated enethers.

Язык: Английский

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Electrochemical N(sp²)–H/C(sp³)–H cross-coupling reaction between sulfoximines and alkylarenes

Green Chemistry, Год журнала: 2024, Номер 26(10), С. 5824 - 5831

Опубликована: Янв. 1, 2024

An electrochemical oxidation-induced amination of simple alkylarenes with sulfoximines as a nitrogen source and 5,6-dimethyl-1 H -benzo[ d ]imidazole catalyst was developed.

Язык: Английский

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Overcoming Challenges in Electrosynthesis Using High‐Throughput Electrochemistry: Hypervalent Iodine‐Mediated Phenol Dearomatization, a Case Study

ChemElectroChem, Год журнала: 2024, Номер 11(13)

Опубликована: Май 2, 2024

Abstract Despite many recent efforts, the field of organic electrosyn‐thesis faces important challenges due to intricate nature heterogeneous redox processes, wide parameter space be explored and lack standardized methods. To overcome these limitations, we developed a cost‐effective high‐throughput electrochemical (HTE) reactor capable running 24 individually controlled parallel reactions. This system allows rapid testing parameters on given reaction, assessing not only yield but also reproducibility. Using hypervalent iodine‐mediated dearomatization phloretic acid as demonstration HTE capabilities, ran more than 200 electrosyntheses in different experimental conditions demonstrate effect such total charge transferred, current, electrode materials, electrolyte formulation concentration, mediator concentration technique oxidation. Notably, this report demonstrates that while catalytic amounts iodine can used successfully, reproducibility may affected, which calls for cautious approach when developing similar transformations. cyclic voltammetry, density functional theory, chronopotentiometry, Raman spectroscopy, shed light causes issue.

Язык: Английский

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