Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2752 - 2906

Published: Aug. 10, 2021

Photoinduced chemical transformations have received in recent years a tremendous amount of attention, providing plethora opportunities to synthetic organic chemists. However, performing photochemical transformation can be quite challenge because various issues related the delivery photons. These challenges barred widespread adoption steps industry. past decade, several technological innovations led more reproducible, selective, and scalable photoinduced reactions. Herein, we provide comprehensive overview these exciting advances, including flow chemistry, high-throughput experimentation, reactor design scale-up, combination photo- electro-chemistry.

Language: Английский

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Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2487 - 2649

Published: Nov. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Language: Английский

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Chemical Aspects of Human and Environmental Overload with Fluorine

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(8), P. 4678 - 4742

Published: March 16, 2021

Over the last 100-120 years, due to ever-increasing importance of fluorine-containing compounds in modern technology and daily life, explosive development fluorochemical industry led an enormous increase emission fluoride ions into biosphere. This made it more important understand biological activities, metabolism, degradation, possible environmental hazards such substances. comprehensive critical review focuses on effects organofluorine (mainly pharmaceuticals agrochemicals) human health environment. To give a better overview, various connected topics are also discussed: reasons trends advance agrochemicals, metabolism fluorinated drugs, withdrawn natural sources organic inorganic fluorine environment (including biosphere), intake, finally biomarkers exposure.

Language: Английский

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Photocatalysis in the Life Science Industry

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2907 - 2980

Published: Sept. 24, 2021

In the pursuit of new pharmaceuticals and agrochemicals, chemists in life science industry require access to mild robust synthetic methodologies systematically modify chemical structures, explore novel space, enable efficient synthesis. this context, photocatalysis has emerged as a powerful technology for synthesis complex often highly functionalized molecules. This Review aims summarize published contributions field from industry, including research industrial-academic partnerships. An overview developed strategic applications synthesis, peptide functionalization, isotope labeling, both DNA-encoded traditional library is provided, along with summary state-of-the-art photoreactor effective upscaling photocatalytic reactions.

Language: Английский

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Contemporary synthetic strategies in organofluorine chemistry

Nature Reviews Methods Primers, Journal Year: 2021, Volume and Issue: 1(1)

Published: July 8, 2021

Language: Английский

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Visible-Light-Driven Catalytic Reductive Carboxylation with CO₂

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(19), P. 10871 - 10885

Published: Aug. 28, 2020

Carbon dioxide (CO2) is an important C1 source for the generation of carboxylic acids and derivatives. Stoichiometric catalytic carboxylation nucleophiles, including organometallic reagents, with CO2 has been widely investigated. Since many kinds reagents are prepared from electrophiles, transition-metal-catalyzed direct diverse electrophiles attracted much attention high step economy user-friendly protocols. Although significant progress achieved, use stoichiometric metallic or pyrophoric reductants common. The renaissance photochemistry seen numerous efforts devoted to light-driven CO2, which become one most active directions in this field. In Perspective, we summarize recent advances visible-light-driven reductive substrates, such as unsaturated hydrocarbons, organic (pseudo)halides, imines, presence mild electron donors, amines, Hantzsch esters, formates. We highlight mechanisms reactions, can proceed absence a photoredox catalyst dual visible light photoredox/transition metal system. also discuss future field offer some insight into challenges that remain.

Language: Английский

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Radiopharmaceuticals for PET and SPECT Imaging: A Literature Review over the Last Decade

International Journal of Molecular Sciences, Journal Year: 2022, Volume and Issue: 23(9), P. 5023 - 5023

Published: April 30, 2022

Positron emission tomography (PET) uses radioactive tracers and enables the functional imaging of several metabolic processes, blood flow measurements, regional chemical composition, and/or absorption. Depending on targeted processes within living organism, different are used for various medical conditions, such as cancer, particular brain pathologies, cardiac events, bone lesions, where most commonly radiolabeled with 18F (e.g., [

Language: Английский

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Direct arene C–H fluorination with ¹⁸ F ⁻ via organic photoredox catalysis

Science, Journal Year: 2019, Volume and Issue: 364(6446), P. 1170 - 1174

Published: June 20, 2019

A metal-free route to PET probes Positron emission tomography (PET) is a widely used imaging technique for medical diagnostics and pharmaceutical development. As the name implies, it requires tracers that emit positrons, typically through labeling with fluorine or carbon radioisotopes. W. Chen et al. devised versatile incorporate radioactive fluoride into aromatic rings. The photochemical method directly substitutes aryl carbon-hydrogen bonds [ 18 F]fluoride so particularly well suited late-stage transformation of complex molecules tracers. Science , this issue p. 1170

Language: Английский

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Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(20), P. 9493 - 9500

Published: May 7, 2020

We report a redox-neutral method for nucleophilic fluorination of N-hydroxyphthalimide esters using an Ir photocatalyst under visible light irradiation. The provides access to broad range aliphatic fluorides, including primary, secondary, and tertiary benzylic fluorides as well unactivated that are typically inaccessible by due competing elimination. In addition, we show the decarboxylative conditions readily adapted radiofluorination with [18F]KF. propose reactions proceed two electron transfers between catalyst redox-active ester substrate afford carbocation intermediate undergoes subsequent trapping fluoride. Examples O- C-centered nucleophiles deoxyfluorination via N-hydroxyphthalimidoyl oxalates also presented, suggesting this approach may offer general blueprint affecting SN1 substitutions mild conditions.

Language: Английский

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Radiochemistry for positron emission tomography

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: June 5, 2023

Abstract Positron emission tomography (PET) constitutes a functional imaging technique that is harnessed to probe biological processes in vivo. PET has been used diagnose and monitor the progression of diseases, as well facilitate drug development efforts at both preclinical clinical stages. The wide applications rapid have ultimately led an increasing demand for new methods radiochemistry, with aim expand scope synthons amenable radiolabeling. In this work, we provide overview commonly chemical transformations syntheses tracers all aspects thereby highlighting recent breakthrough discoveries contemporary challenges field. We discuss use biologicals highlight general examples successful molecular – particular focus on translational scalable radiochemistry concepts entered use.

Language: Английский

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