Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes

Chemistry - A European Journal, Journal Year: 2019, Volume and Issue: 26(15), P. 3241 - 3246

Published: Dec. 25, 2019

Electrophotochemistry has enabled arene C-H trifluoromethylation with the Langlois reagent CF3 SO2 Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for generation radical. electrophotochemistry was carried out in an operationally simple manner, setting stage challenging trifluoromethylations unactivated arenes heteroarenes. robust nature electrophotochemical manifold reflected by wide scope, including electron-rich electron-deficient benzenes, as well naturally occurring Electrophotochemical further achieved flow modular electro-flow-cell equipped in-operando monitoring unit on-line flow-NMR spectroscopy, providing support single electron transfer processes.

Language: Английский

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Visible‐Light‐Enabled Ruthenium‐Catalyzed meta‐C−H Alkylation at Room Temperature

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(29), P. 9820 - 9825

Published: May 10, 2019

Visible-light-induced ruthenium catalysis has enabled remote C-H alkylations with excellent levels of position control under exceedingly mild conditions at room temperature. The metallaphotocatalysis occurred exogenous-photosensitizer-free and features an ample substrate scope. robust nature the photo-induced meta-C-H functionalization is reflected by broad functional group tolerance, reaction can be carried out in operationally simple manner, setting stage for challenging secondary tertiary ruthenaphotoredox catalysis.

Language: Английский

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Flow Rhodaelectro-Catalyzed Alkyne Annulations by Versatile C–H Activation: Mechanistic Support for Rhodium(III/IV)

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(43), P. 17198 - 17206

Published: Sept. 24, 2019

A flow-metallaelectro-catalyzed C–H activation was realized in terms of robust rhodaelectro-catalyzed alkyne annulations. To this end, a modular electro-flow cell with porous graphite felt anode designed to ensure efficient turnover. Thereby, variety C–H/N–H functionalizations proved amenable for annulations high levels regioselectivity and functional group tolerance, viable both an inter- or intramolecular manner. The allowed easy scale up, while in-operando kinetic analysis accomplished by online flow-NMR spectroscopy. Mechanistic studies suggest oxidatively induced reductive elimination pathway on rhodium(III) electrocatalytic regime.

Language: Английский

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Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Feb. 28, 2022

Abstract Biaryl scaffolds are found in natural products and drug molecules exhibit a wide range of biological activities. In past decade, the transition metal-catalyzed C–H arylation reaction came out as an effective tool for construction biaryl motifs. However, traditional reactions have limitations like harsh conditions, narrow substrate scope, use additives etc. therefore encouraged synthetic chemists to look alternate greener approaches. This review aims draw general overview on bond formation C–C bonds with aid different methodologies, majorly highlighting sustainable

Language: Английский

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Visible light-driven C–H arylation of heteroarenes with aryl diazonium salts in water catalyzed by a Z-scheme CuInS₂/K-C₃N₄ heterojunction

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4803 - 4810

Published: Jan. 1, 2024

Z-scheme CuInS 2 /K-C 3 N 4 heterojunction has been designed and confirmed as efficient heterogeneous photocatalyst for arylation of heteroarenes with aryl diazonium salts in water under visible light irradiation to give arylated high yields.

Language: Английский

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Visible-Light-Driven Organic Photochemical Reactions in the Absence of External Photocatalysts

Synthesis, Journal Year: 2019, Volume and Issue: 51(16), P. 3021 - 3054

Published: May 20, 2019

Visible-light-driven organic photochemical reactions have attracted substantial attention from the synthetic community. Typically, catalytic quantities of photosensitizers, such as transition metal complexes, dyes, or inorganic semiconductors, are necessary to absorb visible light and trigger subsequent transformations. Recently, in contrast these photocatalytic processes, a variety photocatalyst-free transformations been exploited for efficient formation carbon–carbon carbon–heteroatom bonds. In addition not requiring additional photocatalysts, they employ low-energy irradiation, mild reaction conditions, enable broad substrate diversity functional group tolerance. This review will focus on summary representative work this field terms different photoexcitation modes. 1 Introduction 2 Visible Light Photoexcitation Single Substrate 3 Reaction Intermediates 4 EDA Complexes between Substrates 5 6 Products 7 Conclusion Outlook

Language: Английский

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Flow Photochemistry as a Tool in Organic Synthesis

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(71), P. 16952 - 16974

Published: May 19, 2020

Abstract Photochemical transformations of molecular building blocks have become an important and widely recognized research field in the past decade. Detailed deep understanding novel photochemical catalysts reaction concepts with visible light as energy source has enabled a broad application portfolio for synthetic organic chemistry. In parallel, continuous‐flow chemistry microreaction technology basis thinking doing fashion clear focus on improved process control higher conversion selectivity. As can be seen by large number scientific publications flow photochemistry recent past, both topics found each other exceptionally well‐suited counterparts high synergy combining technology. This review will give overview selected classes, which represent chemistry, benefit from mild defined conditions transfer batch to mode.

Language: Английский

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Late‐Stage Diversification through Manganese‐Catalyzed C−H Activation: Access to Acyclic, Hybrid, and Stapled Peptides

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(11), P. 3476 - 3480

Published: Dec. 19, 2018

Abstract Bioorthogonal C−H allylation with ample scope was accomplished through a versatile manganese(I)‐catalyzed activation for the late‐stage diversification of structurally complex peptides. The unique robustness manganese(I) catalysis manifold reflected by full tolerance sensitive functional groups, such as iodides, esters, amides, and OH‐free hydroxy thereby setting stage racemization‐free synthesis fused peptide hybrids featuring steroids, drug molecules, natural products, nucleobases, saccharides.

Language: Английский

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Biomass-Derived Solvents for Sustainable Transition Metal-Catalyzed C–H Activation

ACS Sustainable Chemistry & Engineering, Journal Year: 2019, Volume and Issue: 7(9), P. 8023 - 8040

Published: March 29, 2019

Transition metal-catalyzed C–H activation has emerged as an increasingly powerful strategy in molecular syntheses and a particularly attractive alternative to classical methods of cross-couplings. During the recent years, significant focus been dedicated further improve sustainable nature approach. As solvents represent major portion organic pollution caused by chemical syntheses, range nontoxic, biobased, have developed substitute for common reaction media. In this review, we present general perspective biomass-derived transition reactions their unique potential up January 2019.

Language: Английский

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When metal-catalyzed C–H functionalization meets visible-light photocatalysis

Beilstein Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 16, P. 1754 - 1804

Published: July 21, 2020

While aiming at sustainable organic synthesis, over the last decade particular attention has been focused on two modern fields, C-H bond activation, and visible-light-induced photocatalysis. Couplings through activation involve use of non-prefunctionalized substrates that are directly converted into more complex molecules, without need a previous functionalization, thus considerably reduce waste generation number synthetic steps. In parallel, transformations involving photoredox catalysis promote radical reactions in absence initiators. They conducted under particularly mild conditions while using visible light as cheap economic energy source. this way, these strategies follow requirements environment-friendly chemistry. Regarding intrinsic advantages well complementary mode action catalytic previously introduced, their merging synergistic dual system is extremely appealing. perspective, scope review aims to present innovative combining visible-light induced

Language: Английский

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