Recent updates and future perspectives in aziridine synthesis and reactivity

Chem, Год журнала: 2023, Номер 9(7), С. 1658 - 1701

Опубликована: Май 11, 2023

Язык: Английский

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UV Photochromism in Transition Metal Oxides and Hybrid Materials

Small, Год журнала: 2021, Номер 17(32)

Опубликована: Июнь 8, 2021

Abstract Limited levels of UV exposure can be beneficial to the human body. However, radiation present in atmosphere damaging if exceed safe limits which depend on individual skin color. Hence, photochromic materials that respond light by changing their color are powerful tools sense safety limits. Photochromic comprise either organic materials, inorganic transition metal oxides, or a hybrid combination both. The behavior largely relies charge transfer mechanisms and electronic band structures. These factors influenced structure morphology, fabrication, composition, hybridization, preparation among others. Significant challenges involved realizing rapid change, is repeatable, reversible with low fatigue, behaving according desired application requirements. also relate finding right synergy between used, environment it being used for, objectives need achieved. In this review, principles applications processes for oxides photocatalytic applications, outlook context commercialized sensors field presented.

Язык: Английский

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Electrochemical Aziridination of Internal Alkenes with Primary Amines

Chem, Год журнала: 2020, Номер 7(1), С. 255 - 266

Опубликована: Дек. 31, 2020

Язык: Английский

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Kinetic Resolution of Aziridines Enabled by N‐Heterocyclic Carbene/Copper Cooperative Catalysis: Carbene Dose‐Controlled Chemo‐Switchability

Angewandte Chemie International Edition, Год журнала: 2020, Номер 60(6), С. 3268 - 3276

Опубликована: Окт. 26, 2020

Abstract Catalytic kinetic resolution (KR) and dynamic asymmetric transformation (DyKAT) are alternative complementary avenues to access chiral stereoisomers of both starting materials reaction products. The development highly efficient catalytic systems for kinetically controlled processes has therefore been one the linchpins in synthesis. N‐heterocyclic carbene (NHC)/copper cooperative catalysis enabled KR DyKAT racemic N ‐tosylaziridines by [3+3] annulation with isatin‐derived enals, leading enantioenriched ‐tosylaziridine derivatives (up >99 % ee ) a large library spirooxindole high structural diversity stereoselectivity >95:5 d.r., ). Mechanistic studies suggest that NHC can bind reversibly copper catalyst without compromising its activity regulate complex switch chemoselection between DyKAT.

Язык: Английский

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Photocatalytic Carboxylation of C−N Bonds in Cyclic Amines with CO₂ by Consecutive Visible‐Light‐Induced Electron Transfer

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(11)

Опубликована: Янв. 21, 2023

Abstract Visible‐light photocatalytic carboxylation with CO 2 is highly important. However, it still remains challenging for reluctant substrates low reduction potentials. Herein, we report a novel of C−N bonds in cyclic amines via consecutive photo‐induced electron transfer (ConPET). It also the first reductive ring‐opening reaction azetidines, pyrrolidines and piperidines. This strategy practical to transform variety easily available valuable β‐, γ‐, δ‐ ϵ‐amino acids moderate‐to‐excellent yields. Moreover, method features mild transition‐metal‐free conditions, high selectivity, good functional‐group tolerance, facile scalability product derivations. Mechanistic studies indicate that ConPET might be key generating reactive photocatalysts, which enable activation generate carbon radicals carbanions as intermediates.

Язык: Английский

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Aziridination via Nitrogen-Atom Transfer to Olefins from Photoexcited Azoxy-Triazenes

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(14), С. 9499 - 9505

Опубликована: Март 24, 2024

Herein, we report that readily accessible azoxy-triazenes can serve as nitrogen atom sources under visible light excitation for the phthalimido-protected aziridination of alkenes. This approach eliminates need external oxidants, precious transition metals, and photocatalysts, marking a departure from conventional methods. The versatility this transformation extends to selective both activated unactivated multisubstituted alkenes varying electronic profiles. Notably, process avoids formation competing C–H insertion products. described protocol is operationally simple, scalable, adaptable photoflow conditions. Mechanistic studies support idea photofragmentation results in generation free singlet nitrene. Furthermore, mild photoredox-catalyzed N–N cleavage protecting group furnish aziridines reported. Our findings contribute advancement sustainable practical methodologies synthesis nitrogen-containing compounds, showcasing potential broader applications synthetic chemistry.

Язык: Английский

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Organometallic 3d transition metal NHC complexes in oxidation catalysis

Catalysis Science & Technology, Год журнала: 2022, Номер 12(16), С. 4940 - 4961

Опубликована: Янв. 1, 2022

This review summarises the advantages towards catalytic oxidation of most important substrates with 3d transition metal NHC complexes. Additionally activation molecular oxygen by complexes is described.

Язык: Английский

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Aziridine used as a vinylidene unit in palladium-catalyzed [2 + 2 + 1] domino annulation

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(13), С. 3413 - 3420

Опубликована: Янв. 1, 2021

A series of chromone fused methylenecyclopentanes are efficiently constructed in moderate to good yields by Pd-catalyzed [2 + 2 1] annulation, which aziridine is used as a vinylidene unit cleavage two C–N bonds for the first time.

Язык: Английский

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Synthesis of the tris-Amino Acid Labionin through a Contrasteric Aziridination and Ring-Opening Sequence

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 10, 2025

The non-proteinogenic tris-amino acid labionin was discovered in 2010 and since has been described many natural products, defining an entire family of lanthipeptides. unusual amino is biosynthetically produced by the sequential condensation a cysteine onto two dehydroalanines. An attempt 2011 to synthesize monomeric unit unsuccessful yet served as valuable foundation guide present work. A recently disclosed methodology for selective opening aziridines mercaptan nucleophiles applied another contrasteric aziridination, thus enabling short synthesis challenging elusive labionin.

Язык: Английский

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Recent advances in the application of contiguously functionalized aziridines for the synthesis of pharmaceutical precursors via regioselective ring-opening reactions

Molecular Catalysis, Год журнала: 2025, Номер 576, С. 114943 - 114943

Опубликована: Фев. 26, 2025

Язык: Английский

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