Late-stage C–H functionalization offers new opportunities in drug discovery

Nature Reviews Chemistry, Год журнала: 2021, Номер 5(8), С. 522 - 545

Опубликована: Июль 13, 2021

Язык: Английский

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

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2752 - 2906

Опубликована: Авг. 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.

Язык: Английский

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C–H activation

Nature Reviews Methods Primers, Год журнала: 2021, Номер 1(1)

Опубликована: Июнь 17, 2021

Язык: Английский

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

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2487 - 2649

Опубликована: Ноя. 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.

Язык: Английский

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Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2017 - 2291

Опубликована: Ноя. 23, 2021

We present here a review of the photochemical and electrochemical applications multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms which both an proton exchanged together, often concerted elementary step. As such, MS-PCET can function as non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from wide variety common functional groups. introduction practitioner’s guide reaction design, with emphasis on unique energetic selectivity features that characteristic this class. then chapters oxidative N–H, O–H, S–H, C–H homolysis methods, generation corresponding neutral species. Then, reductive PCET activations involving carbonyl, imine, other X═Y π-systems, heteroarenes, where ketyl, α-amino, heteroarene-derived radicals be generated. Finally, we asymmetric catalysis materials device applications. Within each chapter, subdivide by group undergoing homolysis, thereafter type transformation being promoted. Methods published prior end December 2020 presented.

Язык: Английский

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Why Hypothesis Testers Should Spend Less Time Testing Hypotheses

Perspectives on Psychological Science, Год журнала: 2020, Номер 16(4), С. 744 - 755

Опубликована: Дек. 16, 2020

For almost half a century, Paul Meehl educated psychologists about how the mindless use of null-hypothesis significance tests made research on theories in social sciences basically uninterpretable. In response to replication crisis, reforms psychology have focused formalizing procedures for testing hypotheses. These were necessary and influential. However, as an unexpected consequence, psychological scientists begun realize that they may not be ready test Forcing researchers prematurely hypotheses before established sound "derivation chain" between theory is counterproductive. Instead, various nonconfirmatory activities should used obtain inputs make hypothesis informative. Before hypotheses, spend more time forming concepts, developing valid measures, establishing causal relationships concepts functional form those relationships, identifying boundary conditions auxiliary assumptions. Providing these recognized incentivized crucial goal itself. this article, we discuss shifting focus can tie together many loose ends psychology's reform movement help us develop strong, testable theories, urged.

Язык: Английский

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Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

Chemical Reviews, Год журнала: 2021, Номер 121(10), С. 5741 - 5829

Опубликована: Апрель 9, 2021

Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance aryl spanning most disciplines chemical sciences, we review recent development chemistry over past seven years (2013-2020). Special emphasis is put on various new transformations involving generation radical intermediates via thermal, photochemical, and electrochemical means. Recent advances transition metal-catalyzed reactions using also reviewed. Together, these newly developed significantly expand synthetic chemist's repertoire aromatic carbon-carbon carbon-heteroatom bond forming methods precursors, providing powerful tools for synthesis modification complex molecular scaffolds.

Язык: Английский

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A Brief Introduction to Chemical Reaction Optimization

Chemical Reviews, Год журнала: 2023, Номер 123(6), С. 3089 - 3126

Опубликована: Фев. 23, 2023

From the start of a synthetic chemist's training, experiments are conducted based on recipes from textbooks and manuscripts that achieve clean reaction outcomes, allowing scientist to develop practical skills some chemical intuition. This procedure is often kept long into researcher's career, as new developed similar protocols, intuition-guided deviations through learning failed experiments. However, when attempting understand systems interest, it has been shown model-based, algorithm-based, miniaturized high-throughput techniques outperform human intuition optimization in much more time- material-efficient manner; this covered detail paper. As many chemists not exposed these undergraduate teaching, leads disproportionate number scientists wish optimize their reactions but unable use methodologies or simply unaware existence. review highlights basics, cutting-edge, modern well its relation process scale-up can thereby serve reference for inspired each techniques, detailing several respective applications.

Язык: Английский

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Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids**

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(23), С. 9143 - 9148

Опубликована: Март 2, 2020

Abstract As a key element in the construction of complex organic scaffolds, formation C−C bonds remains challenge field synthetic chemistry. Recent advancements single‐electron chemistry have enabled new methods for various bonds. Disclosed herein is development novel reduction acyl azoliums ketones from carboxylic acids. Facile azolium situ followed by radical–radical coupling was made possible merging N‐heterocyclic carbene (NHC) and photoredox catalysis. The utility this protocol synthesis showcased late‐stage functionalization variety pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing advantages over alternative methodologies.

Язык: Английский

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A field guide to flow chemistry for synthetic organic chemists

Chemical Science, Год журнала: 2023, Номер 14(16), С. 4230 - 4247

Опубликована: Янв. 1, 2023

This review explores the benefits of flow chemistry and dispels notion that it is a mysterious “black box”, demonstrating how can push boundaries organic synthesis through understanding its governing principles.

Язык: Английский

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