Modular Access to Chiral Benzylamines via Ni/Photoredox-Catalyzed Multicomponent Cross-Electrophile Coupling

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 30, 2025

A Ni/photoredox dual-catalyzed multicomponent cross-electrophile coupling of N-vinyl amides with (hetero)aryl halides and (2°, 3°)-alkyl redox-active esters in the presence cheap reductant Hantzsch ester is reported here. This reductive protocol provides direct access to various synthetically challenging chiral α-arylamides good yields excellent enantioselectivities (up 99% ee, majority exceeding 97% ee), which can be further derived into primary secondary amines. Preliminary experimental studies shed light on potential catalytic pathways.

Язык: Английский

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Vinylation of Alcohols, Thiols, and Nitrogen Compounds Using a Stoichiometric Amount of In Situ Generated Acetylene

Organics, Год журнала: 2025, Номер 6(1), С. 5 - 5

Опубликована: Фев. 8, 2025

In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of broad scope substances, including alcohols, thiols, nitrogen compounds. The key advantage proposed method is use calcium carbide as robust acetylene source in stoichiometric ratio to substrates. Lacking requirement excess, protocol safe, economic, limits waste production. procedure allows large variety O-,S-,N-vinyl compounds be synthesized up quantitative yields. Our scalable, allowing us obtain vinyl derivatives Gram-scale quantities. We also demonstrated significant synthetic value our approach by performing label-economic synthesis 13C2-labeled using carbide-13C2. well-optimized process, conversion Ca13C2 reached 89%.

Язык: Английский

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

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 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.

Язык: Английский

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Amide and peptide synthesis via nickel-catalyzed cross-electrophile coupling

Cell Reports Physical Science, Год журнала: 2024, Номер unknown, С. 102248 - 102248

Опубликована: Окт. 1, 2024

Язык: Английский

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