Photoredox/Nickel Dual-Catalytic Asymmetric Silylarylation of Alkenes

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 680 - 685

Published: Jan. 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.

Language: Английский

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Nickel‐Catalyzed Asymmetric Reductive 1,4‐ and 1,5‐Dicarbofunctionalization^†

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 8, 2025

Comprehensive Summary Herein, we present the first examples of asymmetric reductive 1,4‐dicarbofunctionalization 1,3‐dienes and 1,5‐dicarbofunctionalization vinylcyclopropanes, which proceed under catalysis a chiral nickel/bis‐imidazoline complex using alkyl halides aryl iodides or alkenyl bromides as electrophilic coupling partners. In these highly enantioselective transformations operating in radical relay mechanism, C(sp 3 )‐ 2 )‐type carbo‐moieties are respectively installed on terminal internal position with newly formed olefinic unit high E ‐selectivity.

Language: Английский

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Three-Component 1,2-Carboalkynylation of Alkenes Via Cooperative Nickel/Photoredox Catalysis

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

A photoredox/nickel dual catalytic system was developed for the three-component 1,2-carboalkynylation of alkenes. This redox-neutral protocol enables efficient and divergent synthesis aliphatic alkynes in high yields with excellent regioselectivity, using readily available starting materials. The resulting adducts can be transformed into terminal alkynes, facilitating diverse downstream transformations. Mechanistic studies were performed to elucidate preferred pathway this alkene difunctionalization process.

Language: Английский

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

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7833 - 7841

Published: April 25, 2025

Language: Английский

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Nickel/Photoredox Dual-Catalyzed, Regioselective 1,2-Carboacylation of Alkenes via Synergistic Alkyl and Benzoyl Radical Coupling

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 2, 2025

A regioselective 1,2-carboacylation protocol of alkenes via nickel/photoredox dual catalysis has been successfully developed under mild conditions. wide range alkyl bromides, α-oxocarboxylic acids, and styrenes proved to be compatible the optimized conditions, affording corresponding products in up 91% yields. Mechanistically, key success this approach is temporal orchestration radical generation: nickel-catalyzed halogen atom transfer (XAT) for bromides photoredox-driven decarboxylation acids.

Language: Английский

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