Native Amides as Enabling Vehicles for Forging sp³–sp³ Architectures via Interrupted Deaminative Ni-Catalyzed Chain-Walking

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(7), P. 3869 - 3874

Published: Feb. 8, 2023

Herein, we disclose an interrupted deaminative Ni-catalyzed chain-walking strategy that forges sp3-sp3 architectures at remote, yet previously unfunctionalized, methylene sp3 C-H sites enabled by the presence of native amides. This protocol is characterized its mild conditions and wide scope, including challenging substrate combinations. Site-selectivity can be dictated a judicious choice ligand, thus offering opportunity to enable bond formations are otherwise inaccessible in conventional events.

Language: Английский

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Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(28)

Published: May 5, 2023

The aryl-to-vinyl nickel 1,4-migration (1,4-Ni migration) reaction has been reported for the first time. generated alkenyl Ni species undergo a reductive coupling with unactivated brominated alkanes affording series of trisubstituted olefins. This tandem exhibits mild conditions, broad substrate scope, high regioselectivity, and excellent Z/E stereoselectivity. A controlled experiments have shown that critical 1,4-Ni migration process is reversible. In addition, intermediates obtained after are highly stereoselective do not isomerization. trace isomerization products caused by instability product.

Language: Английский

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Silanes as a versatile hydride source for Ni–H catalysis: a promising tool for π-hydro functionalization

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4290 - 4317

Published: Jan. 1, 2024

Nickel-catalyzed hydrofunctionalization of π-substrates is a possibly effective method to synthesize several value-added molecular architectures. This review covers the NiH catalyzed reactions alkenes, alkynes and allenes.

Language: Английский

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Hydrodeuteroalkylation of Unactivated Olefins Using Thianthrenium Salts

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(36)

Published: June 13, 2024

Isotopically labeled alkanes play a crucial role in organic and pharmaceutical chemistry. While some deuterated methylating agents are readily available, the limited accessibility of other deuteroalkyl reagents has hindered synthesis corresponding products. In this study, we introduce nickel-catalyzed system that facilitates various deuterium-labeled through hydrodeuteroalkylation d2-labeled alkyl TT salts with unactivated alkenes. Diverging from traditional reagents, thianthrenium (TT) can effectively selectively deuterium at α position chains using D

Language: Английский

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Nickel-Catalyzed, Enantioselective Hydrofluoromethylation of Olefins: Access to Chiral α-Fluoromethylated Amides and Esters

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2218 - 2222

Published: March 24, 2023

We herein report the nickel-catalyzed enantioselective hydrofluoromethylation of enamides and enol esters with CH2FI as fluoromethyl source to enable diversity-oriented synthesis (DOS) chiral α-fluoromethylated amides well features wide functional group compatibility excellent enantioselectivity. The synthetic value this protocol was demonstrated by transformations resulted different scaffolds including amine, oxazoline, thiazoline, tetrahydroquinoline.

Language: Английский

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C—F Bond Insertion into Indoles with CHBr₂F: An Efficient Method to Synthesize Fluorinated Quinolines and Quinolones

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(10), P. 1128 - 1132

Published: Feb. 6, 2024

Comprehensive Summary A mild and practical method for synthesizing fluorinated quinoline derivatives, which have a wide range of applications in pharmaceuticals, materials, organic synthesis, was described through C—F bond insertion into indoles using CHBr 2 F. The simple conditions, readily availability F, as well the versatility transformations make this strategy very powerful 3‐fluoroquinoline 3‐fluoroquinolone. mechanistic studies reveal that bromofluorocarbene generated in‐situ under basic condition key intermediate.

Language: Английский

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An Oxidative [3+2+1] Cyclization of Enaminones and N‐Alkenyl‐2‐pyrrolidinone: Access to Polysubstituted 4‐Alkylated 1,4‐dihydropyridines

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(8), P. 1217 - 1223

Published: March 25, 2023

Abstract An oxidative [3+2+1] cyclization of enaminones and N ‐alkenyl‐2‐pyrrolidinone is described for the synthesis 4‐alkylated 1,4‐dihydropyridines (1,4‐DHPs). By using terminal olefin as C4 source 1,4‐DHP skeleton, this synthetic strategy provides a series 1,4‐DHPs through 1,1‐difunctionalization/cyclization process. In protocol, two C( sp 3 )−C( 2 ) bonds )−N bond are simultaneously formed, hydrogen on newly formed methyl group skeleton confirmed possible mechanism proposed. magnified image

Language: Английский

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Recent Progress in NiH-Catalyzed Linear or Branch Hydrofunctionalization of Terminal or Internal Alkenes

Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(5)

Published: July 20, 2023

Language: Английский

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Nickel-Catalyzed Synthesis of Fluorine-Bearing Silane through Halofluoroalkylation and Hydrofluoroalkylation of Alkenylsilanes

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100129 - 100129

Published: April 1, 2025

Language: Английский

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aPolyoxovanadate-based MOFs: Multi-site Efficient Catalytic Epoxidation of Olefins

Journal of Alloys and Compounds, Journal Year: 2025, Volume and Issue: unknown, P. 179861 - 179861

Published: March 1, 2025

Language: Английский

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