Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

Chemical Reviews, Год журнала: 2022, Номер 122(6), С. 6634 - 6718

Опубликована: Фев. 18, 2022

Organic compounds labeled with hydrogen isotopes play a crucial role in numerous areas, from materials science to medicinal chemistry. Indeed, while the replacement of by deuterium gives rise improved absorption, distribution, metabolism, and excretion (ADME) properties drugs enables preparation internal standards for analytical mass spectrometry, use tritium-labeled is key technique all along drug discovery development pharmaceutical industry. For these reasons, interest new methodologies isotopic enrichment organic molecules extent their applications are equally rising. In this regard, Review intends comprehensively discuss developments area over last years (2017–2021). Notably, besides fundamental isotope exchange (HIE) reactions isotopically analogues common reagents, plethora reductive dehalogenative deuteration techniques other transformations incorporation emerging now part labeling toolkit.

Язык: Английский

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Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Chemical Society Reviews, Год журнала: 2020, Номер 50(2), С. 766 - 897

Опубликована: Дек. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Язык: Английский

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Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2353 - 2428

Опубликована: Окт. 8, 2021

For more than 70 years, nitrogen-centered radicals have been recognized as potent synthetic intermediates. This review is a survey designed for use by chemists engaged in target-oriented synthesis. summarizes the recent paradigm shift access to and application of N-centered enabled visible-light photocatalysis. broadens streamlines approaches many small molecules because photocatalysis conditions are mild. Explicit attention paid innovative advances N–X bonds radical precursors, where X = Cl, N, S, O, H. clarity, key mechanistic data noted, available. Synthetic applications limitations summarized illuminate tremendous utility photocatalytically generated radicals.

Язык: Английский

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Phosphorus-Based Catalysis

ACS Central Science, Год журнала: 2021, Номер 7(4), С. 536 - 558

Опубликована: Март 16, 2021

Phosphorus-based organocatalysis encompasses several subfields that have undergone rapid growth in recent years. This Outlook gives an overview of its various aspects. In particular, we highlight key advances three topics: nucleophilic phosphine catalysis, organophosphorus catalysis to bypass oxide waste, and compound-mediated single electron transfer processes. We briefly summarize five additional chiral phosphoric acid Lewis base iminophosphorane super phosphonium salt phase frustrated pair catalysis. Although it is not catalytic nature, also discuss novel discoveries are emerging phosphorus(V) ligand coupling. conclude with some ideas about the future

Язык: Английский

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Photogenerated acyl/alkoxycarbonyl/carbamoyl radicals for sustainable synthesis

Green Chemistry, Год журнала: 2019, Номер 21(4), С. 748 - 764

Опубликована: Янв. 1, 2019

Recent examples of sustainable acylations by photogenerated acyl/alkoxycarbonyl/carbamoyl radicals have been discussed in this article.

Язык: Английский

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C–H deuteration of organic compounds and potential drug candidates

Chemical Society Reviews, Год журнала: 2022, Номер 51(8), С. 3123 - 3163

Опубликована: Янв. 1, 2022

This review summarises deuteration methods of various organic motifs containing C(sp 2 )−H and 3 bonds utilizing C−H bond functionalisation as a key step along with variety catalysts, exemplifies their biological relevance.

Язык: Английский

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Phosphoranyl Radical Fragmentation Reactions Driven by Photoredox Catalysis

ACS Catalysis, Год журнала: 2020, Номер 10(13), С. 7250 - 7261

Опубликована: Июнь 5, 2020

Photocatalytic generation of phosphoranyl radicals is fast emerging as an essential method for the diverse and valuable radicals, typically via deoxygenation or desulfurization processes. This Perspective a comprehensive evaluation all studies using tunable mediators in photoredox catalysis, highlighting how two distinct methods radical formation (radical addition nucleophilic addition) can be used to generate versatile intermediates with reactivity profiles.

Язык: Английский

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Photocatalytic, Phosphoranyl Radical-Mediated N–O Cleavage of Strained Cycloketone Oximes

Organic Letters, Год журнала: 2019, Номер 21(8), С. 2658 - 2662

Опубликована: Апрель 3, 2019

A photoinduced, phosphoranyl radical-mediated protocol for the direct N–O cleavage of strained cycloketone oximes via a polar/SET crossover process was developed first time. This visible-light-driven activation mode oxime offers beneficial features such as streamlined synthetic and versatile photochemical reactivities. Consequently, alkenes α-trifluoromethyl with varied electronic structural acted competent radical receptors in this protocol, enabling facile accesses to range elongated cyano and/or gem-difluoroalkene-bearing compounds.

Язык: Английский

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Radical deuteration

Chemical Society Reviews, Год журнала: 2022, Номер 51(15), С. 6291 - 6306

Опубликована: Янв. 1, 2022

This review is a systematic summary of radical deuteration with four reaction types: reductive deuteration, defunctionalization–deuteration, hydrogen–deuterium (H/D) exchange and deuteroalkylation.

Язык: Английский

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Highly selective synthesis of all-carbon tetrasubstituted alkenes by deoxygenative alkenylation of carboxylic acids

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Фев. 4, 2022

Abstract The synthesis of all-carbon tetrasubstituted olefins under mild reaction conditions is challenging because the inevitable issues including significant steric hindrance and uncontrolled Z/E stereoselectivity. In this paper, we report alkenes from readily available carboxylic acids alkenyl triflates with synergistic catalysis cyclo-octa-1,5-diene(tetramethyl-1,4-benzoquinone)nickel visible light an air atmosphere, thus avoiding need for a glovebox or Schlenk line. A wide range aromatic cyclic acyclic undergo C-C coupling process smoothly, forming structurally diverse stereospecifically in moderate to good yields. practicality method further illustrated by late-stage modification complex molecules, one pot gram-scale applications. This important step towards valuable utilization acids, it also simplifies experimental operation metallophotoredox moisture sensitive nickel(0) catalysis.

Язык: Английский

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