Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(4), P. 1364 - 1416

Published: Jan. 17, 2023

Hypervalent aryliodoumiums are intensively investigated as arylating agents. They excellent surrogates to aryl halides, and moreover they exhibit better reactivity, which allows the corresponding arylation reactions be performed under mild conditions. In past decades, acyclic aryliodoniums widely explored However, unmet need for is improvement of their notoriously low reaction economy because coproduced iodides during often wasted. Cyclic have intrinsic advantage in terms economy, started receive considerable attention due valuable synthetic applications initiate cascade reactions, can enable construction complex structures, including polycycles with potential pharmaceutical functional properties. Here, we summarizing recent advances made research field cyclic aryliodoniums, nascent design aryliodonium species applications. First, general preparation typical diphenyl iodoniums described, followed by heterocyclic monoaryl iodoniums. Then, initiated arylations coupled subsequent domino summarized construct polycycles. Meanwhile, building biaryls axial atropisomers discussed a systematic manner. Finally, very advance employed halogen-bonding organocatalysts described.

Language: Английский

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Platinum group metal (PGM) complexes having acylthiourea ligand system as catalysts or anticancer agents

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 503, P. 215620 - 215620

Published: Jan. 8, 2024

Language: Английский

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(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(36)

Published: July 14, 2022

Azepanes are important seven-membered heterocycles, which present in numerous natural and synthetic compounds. However, the development of convergent methods to access them remains challenging. Herein, we report Lewis acid catalyzed (4+3) annulative addition aryl amino donor-acceptor cyclopropanes with 2-aza-1,3-dienes. Densely substituted azepane derivatives were obtained good excellent yields high diastereoselectivity. The reaction occurred under mild conditions ytterbium triflate as catalyst. use copper a trisoxazoline (Tox) ligand led an enantioselective transformation. cycloadducts convenient substrates for series further modifications, showing utility these

Language: Английский

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Nickel-catalyzed hydroarylation reaction: a useful tool in organic synthesis

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(18), P. 5074 - 5103

Published: Jan. 1, 2022

The nickel-catalyzed hydroarylation reaction opens up new routes to access complex organic compounds in a highly regio and stereoselective fashion from easily available precursors, such as olefin, alkyne, arene, aryl halide, boronic acid.

Language: Английский

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The synthesis of seven- and eight-membered rings by radical strategies

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4757 - 4781

Published: Jan. 1, 2022

Radical strategies for preparation of seven- or eight-membered rings.

Language: Английский

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Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(4), P. 1045 - 1045

Published: Jan. 1, 2024

Transition-metal-catalyzed cycloadditions have been evolved as important and efficient methods to construct cyclic molecules.Among them, transition-metal-catalyzed using carbon monoxide (CO) gas the 1C synthon provide their unique powerful approaches build various molecules within a carbonyl group, which either acts an functional group cycloadducts, or can be further elaborated other groups.The tremendous advances in this field are introduced.

Language: Английский

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Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(40), P. 16709 - 16717

Published: Oct. 4, 2021

Crystallographic characterization of RuX(CO)(η3-C3H5)(JOSIPHOS), where X = Cl, Br, or I, reveals a halide-dependent diastereomeric preference that defines metal-centered stereogenicity and, therefrom, the enantioselectivity C−C coupling in ruthenium-catalyzed anti-diastereo- and enantioselective couplings primary alcohols with 1-aryl-1-propynes to form products carbonyl anti-(α-aryl)allylation. Computational studies reveal non-classical hydrogen bond between iodide aldehyde formyl CH stabilizes favored transition state for addition. An improved catalytic system enabling previously unattainable transformations was developed employs an iodide-containing precatalyst, RuI(CO)3(η3-C3H5), combination trifluoroethanol, as illustrated by first ethanol higher alcohols.

Language: Английский

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Photoredox‐Enabled Manganese‐Catalyzed [2+2+2] Cycloaddition of Alkynes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1545 - 1550

Published: Feb. 8, 2024

Abstract Manganese (Mn) is the third most abundant transition metal on Earth and known for its exceptional biocompatibility. The development of novel catalytic mode Mn great significance to advancing organic synthesis. In this study, first manganese (Mn)‐catalyzed [2+2+2] cycloaddition alkynes achieved with aid visible‐light photoredox catalysis. Photoredox catalysis proposed promote transformation by in situ reduction high‐valent Mn(II) complex Mn(0) species, thereby initiating reaction. Additionally, a photooxidation‐induced reductive ellimination step also suggested. This system further distinguished notable tolerance towards both terminal internal as counterparts diynes.

Language: Английский

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Utilization of ruthenium(0) for σ-bond activation: Formation of organoruthenium complexes and emergence of their catalytic activity via in situ Ru-C bond cleavage

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123567 - 123567

Published: Feb. 1, 2025

Language: Английский

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Synthesis of Dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The first asymmetric synthesis of (-)-dihydrogambirtannine has been achieved using nucleophilic addition to a chiral sulfinyl imine establish the stereogenic centre and [2 + 2 2] alkyne cyclotrimerisation construct aromatic E ring.

Language: Английский

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