Regio- and Stereoselective Intermolecular 1,2-Difunctionalization of Terminal Alkynes: An Approach to Access (Z)-β-Amidovinylsulfones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 2873 - 2884

Опубликована: Фев. 14, 2024

We have developed the first I2/base-catalyzed regio- and stereoselective intermolecular β-amidosulfonylation of terminal alkynes using sodium sulfinates quinoxalinone derivatives. The present methodology is compatible with a broad spectrum various heterocyclic amides, alkynes, sulfinates. It provides rapid access to valuable (Z)-β-amidovinyl sulfones at mild conditions. Moreover, synthetic application this was demonstrated by late-stage functionalization numerous bioactive molecules.

Язык: Английский

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CoH-catalyzed asymmetric remote hydroalkylation of heterocyclic alkenes: a rapid approach to chiral five-membered S- and O-heterocycles

Chemical Science, Год журнала: 2024, Номер 15(23), С. 8888 - 8895

Опубликована: Янв. 1, 2024

A highly efficient method achieves precise construction of alkyl chiral centers at remote C3-positions in five-membered S/O-heterocycles via cobalt-catalyzed asymmetric hydroalkylation heterocyclic alkenes.

Язык: Английский

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Traceless Nucleophile Strategy for C5‐Selective C–H Sulfonylation of Pyridines

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(47)

Опубликована: Авг. 10, 2024

Abstract The functionalization of pyridines is crucial for the rapid construction and derivatization agrochemicals, pharmaceuticals, materials. Conventional approaches have primarily focused on ortho ‐ para ‐positions, while achieving precise meta‐selective functionalization, particularly at C5 position in substituted pyridines, remains a formidable challenge due to intrinsic electronic properties pyridines. Herein, we present new strategy meta C5‐selective C−H sulfonylation N ‐amidopyridinium salts, which employs transient enamine‐type intermediate generated through nucleophilic addition salts. This process harnesses power electron donor‐acceptor complexes, enabling high selectivity broad applicability, including complex bearing valuable sulfonyl functionalities under mild conditions without need an external photocatalyst. remarkable selectivity, combined with applicability late‐stage significantly expands toolbox pyridine unlocking access previously unattainable ‐sulfonylated

Язык: Английский

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Ni-catalyzed enantioselective three-component reductive alkylacylation of alkenes: modular access to structurally complex α-amino ketones

Chemical Science, Год журнала: 2024, Номер 15(37), С. 15489 - 15495

Опубликована: Янв. 1, 2024

Nickel-catalyzed three-component reductive dicarbofunctionalization of activated olefins (enamides) is presented.

Язык: Английский

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Photoredox/Nickel Dual-Catalytic Asymmetric Silylarylation of Alkenes

Organic Letters, Год журнала: 2025, Номер 27(2), С. 680 - 685

Опубликована: Янв. 6, 2025

The efficient construction of chiral aryl-containing organosilicon frameworks via catalytic enantioselective three-component silylarylation alkenes remains a great challenge. Herein, photoredox/nickel dual-catalytic asymmetric protocol has been disclosed by using biimidazoline (BiIM) as the ligand, silylboranes silyl radical precursors, aryl bromides coupling partners, and morpholine promoter. Remarkably, reaction features mild green conditions, high efficiency, excellent enantioselectivity, enabling facile synthesis valuable tropic acid sila-isoflavanone structures.

Язык: Английский

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Ni-Catalyzed Regioselective and Site-divergent Reductive Arylalkylations of Allylic Amines

Chemical Science, Год журнала: 2025, Номер 16(10), С. 4442 - 4449

Опубликована: Янв. 1, 2025

Catalytic methods by switching the least parameters for regioselective and site-divergent transformations to construct different architectures from identical readily available starting materials are among most ideal catalytic protocols. However, associated challenge precisely control both regioselectivity site diversity renders this strategy appealing yet challenging. Herein, Ni-catalyzed cross-electrophile 1,2- 1,3-arylalkylations of N-acyl allylic amines have been developed. This reductive three-component protocol enables 1,2-arylalkylation 1,3-arylalkylation with aryl halides alkyl excellent chemo-, regio- site-selectivity, representing first example controlled migratory difunctionalization alkenes under conditions. A wide range terminal internal unactivated amines, precursors were tolerated, providing straightforward efficient access diverse C(sp3)-rich branched aliphatic materials.

Язык: Английский

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Harnessing visible light for alkenylation reactions: A promising strategy in organic synthesis

Molecular Catalysis, Год журнала: 2025, Номер 579, С. 115028 - 115028

Опубликована: Март 22, 2025

Язык: Английский

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Nickel-Catalyzed Enantioselective Three-Component 1,2-Alkylarylation of Alkenes with Arylboronic Acids as Arylation Reagents

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 7833 - 7841

Опубликована: Апрель 25, 2025

Язык: Английский

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Recent Advances in Photochemical Asymmetric Three‐Component Reactions

The Chemical Record, Год журнала: 2023, Номер 23(12)

Опубликована: Сен. 29, 2023

Abstract Over the past decades, asymmetric photochemical synthesis has garnered significant attention for its sustainability and unique ability to generate enantio‐enriched molecules through distinct reaction pathways. Photochemical three‐component reactions have demonstrated potential rapid construction of chiral compounds with molecular diversity complexity. However, noteworthy challenges persist, including participation high‐energy intermediates such as radical species, difficulties in precise control stereoselectivity, presence competing background side reactions. Recent breakthroughs led development sophisticated strategies this field. This review explores intricate mechanisms, synthetic applications, limitations these methods. We anticipate that it will contribute towards advancing catalysis, synthesis, green chemistry.

Язык: Английский

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Catalytic Enantioselective Electrophilic Difunctionalization of Unsaturated Sulfones

Organic Letters, Год журнала: 2024, Номер 26(21), С. 4514 - 4519

Опубликована: Май 17, 2024

An efficient protocol of enantioselective thiolative azidation sulfone-tethered alkenes via a chiral chalcogenide catalyzed electrophilic reaction is disclosed. A series enantioenriched sulfones bearing remote stereogenic centers was achieved with good yields and high enantioselectivities linear unsaturated cyclic sulfones. Mechanistic studies revealed the importance sulfone group in improvement reactivity enantioselectivity reaction.

Язык: Английский

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