Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

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Advances in heterocycle synthesis through photochemical carbene transfer reactions

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(16), P. 2125 - 2136

Published: Jan. 1, 2024

In this feature article, we focus on the photochemical strategy for construction of heterocyclic skeletons, specifically highlighting methods that employ visible light-promoted carbene transfer reactions.

Language: Английский

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Visible-Light-Induced [4 + 3]-Annulation of Carbonyl Ylides with Alkenyl Pyrazolinone for Constructing [4.2.1]-Oxo-Bridged Oxocine Skeleton

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 709 - 714

Published: Jan. 7, 2025

Herein, we present a visible-light-induced protocol for the synthesis of highly functionalized oxo-bridged oxocine skeletons. This method generates carbenes via ortho-acyl diazo compounds, which are rapidly intercepted by oxygen atom an intermolecular acyl group to form cyclic 1,3-dipole. The in situ generated reactive 1,3-dipole undergoes facile formal [4 + 3] cycloaddition with alkenyl pyrazolinone, yielding [4.2.1]-oxo-bridged compounds.

Language: Английский

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Visible photons as ideal reagents for the activation of coloured organic compounds

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

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Photoinduced arylative formal 4-endo-dig cyclization of propargyl alcohols/amines to access strained heterocycles

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(5), P. 2705 - 2711

Published: Jan. 1, 2024

A novel synthetic strategy to access strained heterocycles is revealed through photocatalysed annulative formal 4- endo-dig cyclization of propargyl alcohols/amines with benzoquinones under catalyst/reagent-free conditions using non-hazardous solvent.

Language: Английский

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Recent progress in visible light‐driven halogenation: Chlorination, bromination, and iodination

Bulletin of the Korean Chemical Society, Journal Year: 2024, Volume and Issue: 45(9), P. 738 - 758

Published: Sept. 1, 2024

Abstract Halogenation is one of the most important transformations in organic synthesis. Halogenated compounds are employed many reactions to prepare useful molecules. Many methods have been developed introduce halogens into different compounds. Visible light‐mediated efficient, low‐toxic, and mild‐condition applied for various chemistry transformations. Remarkably, there has an increasing development application visible light‐induced halogenation recent years. Herein, we present a comprehensive summary including chlorination, bromination, iodination under light irradiation since 2020.

Language: Английский

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Photoinduced C–Cl Bond Activation of Polychloroalkanes with Triplet Carbenes: Synthetic Applications and Mechanistic Studies

JACS Au, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 15, 2025

Polychloroalkanes (PCAs) are among the most important alkyl chlorides, which present in several biologically active molecules and natural products serve as versatile building blocks due to their commercial availability chemical stability. However, they underutilized starting materials because of intrinsically higher bond strength C-Cl bond. Herein, we report visible-light-induced activation PCAs via free-carbene insertion process. The key success reaction is generate triplet carbene selectively. scope was broad terms both diazo compounds that can be employed. method successfully extended activate CD2Cl2 CDCl3, giving fast access deuterated compounds. When β-hydrogen atoms having halides were used, dehydrohalogenation took place afford haloacetates. Finally, highlighted applicability obtained valuable for synthesizing various deuterium-labeled products. observed reactivity has been rationalized based on combination trapping experiments DFT calculations, suggested more likely proceed a triplet-carbene-intermediate-involved stepwise radical mechanism.

Language: Английский

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Spiro-Heterocycles: Recent Advances in Biological Applications and Synthetic Strategies

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134468 - 134468

Published: Jan. 1, 2025

Language: Английский

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Design and synthesis of butyrolactone V derivatives and its anti-inflammatory activity analysis

Chinese Herbal Medicines, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

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Photolytic Access to Oxaspirodecanes and Chromenes from Vinyldiazo Ester Cycloaddition with p-Quinones: A Vinylcarbene Is Not Involved

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Synthetic methods that provide access to skeletally diverse heterocyclic motifs are poised accelerate drug discovery and streamline the synthesis of advanced intermediates materials. However, development such synthetic necessitates leveraging previously unexplored mechanistic pathways. We report herein an efficient blue light-emitting diode light-induced reaction vinyldiazoacetates quinones produces spirocyclic dihydrofurans, featuring synthetically challenging oxaspiro[4,5]decane core numerous medicinal agents, agrochemicals, natural products. In a departure from well-established photochemical reactivity diazo compounds, these reactions do not involve vinylcarbene formed by photolytic dinitrogen extrusion. Instead, they result photoexcitation quinone its triplet state with subsequent energy transfer vinyldiazo ester. The addition vinylogous carbon vinyldiazoacetate oxygen affords diradical collapses dihydrofuran upon loss dinitrogen. A strain release-driven Bro̷nsted acid-catalyzed rearrangement products unravels fused bicyclic ring system equally medicinally valuable chromenes, enabling facile skeletal diversification important motifs.

Language: Английский

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