Organic thermally activated delayed fluorescence (TADF) compounds used in photocatalysis

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(13), P. 7587 - 7680

Published: Jan. 1, 2021

Organic compounds that show Thermally Activated Delayed Fluorescence (TADF) have become wildly popular as next generation emitters in organic light-emitting diodes (OLEDs), but since 2016, received significant and increasing attention photocatalysts.

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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Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(3), P. 1640 - 1683

Published: Jan. 20, 2021

The past decade has witnessed the emergence of N-(acyloxy)phthalimides (NHPI esters) and its derivatives at forefront synthetic methods facilitating construction diverse molecular frameworks from readily available carboxylic acid feedstock. NHPI esters are predisposed to undergo reductive fragmentation via a single electron transfer (SET) process under thermal, photochemical, or electrochemical conditions generate corresponding carbon- nitrogen-centered radicals that participate in multitude transformations forge carbon–carbon carbon–heteroatom bonds. chemistry involving received broad applicability not only well-designed cascade annulations but also medicinal natural product synthesis. This comprehensive Review, broadly categorized according nature bond formation, details progress made this field since initial discovery by providing representative examples with mechanistic details, an emphasis on challenges future directions.

Language: Английский

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Decarboxylative Halogenation of Organic Compounds

Chemical Reviews, Journal Year: 2020, Volume and Issue: 121(1), P. 412 - 484

Published: Nov. 17, 2020

Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for synthesis ubiquitous organic halides. The method is based on conversion carboxylic acids to corresponding halides via selective cleavage a carbon-carbon bond between skeleton molecule and group liberation carbon dioxide. In this review, we discuss analyze major approaches alkanoic, alkenoic, acetylenic, (hetero)aromatic alkyl, alkenyl, alkynyl, (hetero)aryl These include preparation families valuable iodides, bromides, chlorides, fluorides. historic modern halodecarboxylation reactions are broadly discussed, including analysis their advantages drawbacks. We critically address features, reaction selectivity, substrate scopes, limitations approaches. available cases, mechanistic details presented, generality uniqueness different pathways highlighted. challenges, opportunities, future directions in field decarboxylative halogenation provided.

Language: Английский

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A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation

Science, Journal Year: 2021, Volume and Issue: 374(6572), P. 1258 - 1263

Published: Dec. 2, 2021

Bimolecular homolytic substitution (S

Language: Английский

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Visible Light Assisted Radical‐Polar/Polar‐Radical Crossover Reactions in Organic Synthesis

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(13), P. 3146 - 3169

Published: April 10, 2021

Abstract Chemists are generally familiar with polar reactions and radical reactions, in comparison, underdeveloped. In the last few years, however, novel concept of amalgamation above two form radical‐polar crossover (RPCO) polar‐radical (PRCO) has emerged as a valuable powerful tool. This methodology tends to bridge gap between well overcomes limitations both traditional chemistry. By bringing together unorthodox chemistry radicals orthodox carbocations carbanions, green quotient such is significantly improved. The development shaping up this area years synthetically important transformations summarised review. magnified image

Language: Английский

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A Triple Photoredox/Cobalt/Brønsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(18), P. 7953 - 7959

Published: April 27, 2022

We demonstrate Markovnikov hydroalkoxylation of unactivated alkenes using alcohols through a triple catalysis consisting photoredox, cobalt, and Brønsted acid catalysts under visible light irradiation. The realizes three key elementary steps in single catalytic cycle: (1) Co(III) hydride generation by photochemical reduction Co(II) followed protonation, (2) metal hydrogen atom transfer (MHAT) hydride, (3) oxidation the alkyl complex to Co(IV). precise control protons electrons allows elimination strong acids external reductants/oxidants that are required conventional methods.

Language: Английский

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Strategies for Nucleophilic C(sp³)–(Radio)Fluorination

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(18), P. 9928 - 9950

Published: April 24, 2023

This Perspective surveys the progress and current limitations of nucleophilic fluorination methodologies. Despite long rich history C(sp3)–F bond construction in chemical research, inherent challenges associated with this transformation have largely constrained to a privileged reaction platform. In recent years, Doyle group─along many others─has pursued study development intent generating deeper mechanistic understanding, developing user-friendly reagents, contributing invention synthetic methods capable enabling radiofluorination. Studies from our laboratory are discussed along developments others field. Fluoride reagent implications identity highlighted. We also outline space inaccessible by technologies series future directions field that can potentially fill existing dark spaces.

Language: Английский

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Iron-mediated modular decarboxylative cross-nucleophile coupling

Chem, Journal Year: 2023, Volume and Issue: 9(6), P. 1610 - 1621

Published: May 4, 2023

Language: Английский

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Co-Catalyzed Hydrofluorination of Alkenes: Photocatalytic Method Development and Electroanalytical Mechanistic Investigation

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(7), P. 4380 - 4392

Published: Feb. 1, 2024

The hydrofluorination of alkenes represents an attractive strategy for the synthesis aliphatic fluorides. This approach provides a direct means to form C(sp3)–F bonds selectively from readily available alkenes. Nonetheless, conducting using nucleophilic fluorine sources poses significant challenges due low acidity and high toxicity associated with HF poor nucleophilicity fluoride. In this study, we present new Co(salen)-catalyzed simple utilizing Et3N·3HF as sole source both hydrogen fluorine. process operates via photoredox-mediated polar-radical-polar crossover mechanism. We also demonstrated versatility method by effectively converting diverse array activated varying degrees substitution into hydrofluorinated products. Furthermore, successfully applied methodology 18F-hydrofluorination reactions, enabling introduction 18F potential radiopharmaceuticals. Our mechanistic investigations, conducted rotating disk electrode voltammetry DFT calculations, unveiled involvement carbocation CoIV–alkyl species viable intermediates during fluorination step, contribution each pathway depends on structure starting alkene.

Language: Английский

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