Electrochemical formylation of aryl halides by using DMF as formyl source DOI

Congcong Qiang,

Mengyun Wu,

Jingru Han

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An electrochemical protocol for the formylation of aryl halides by using DMF as a formyl source was developed to produce aromatic aldehydes in moderate good yields.

Language: Английский

Red-Light Mediated Formylation of Indoles Using Helical Carbenium Ion as Photoredox Catalyst DOI

Nand Lal,

Deepshikha Deepshikha,

P. R. SINGH

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A red-light ( λ = 640 nm)-mediated C-3 formylation of indoles utilizing a helical carbenium ion as photocatalyst and 2,2-dimethoxy- N , -dimethylethanamine formylating source is presented.

Language: Английский

Citations

1
Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides DOI

Ke-Rong Li,

Xian‐Chen He,

Jie Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12658 - 12667

Published: Aug. 19, 2024

Nickel/photoredox catalysis has emerged as a powerful platform for exploring nontraditional and challenging cross-couplings. Herein, metallaphotoredox catalytic protocol been developed on the basis of tertiary amine-ligated boryl radical-induced halogen atom transfer process under blue-light irradiation. A wide variety aryl heteroaryl bromides featuring different functional groups pharmaceutical moieties were facilely coupled to rapidly install C(sp3)-enriched aromatic scaffolds. The compatibility Lewis base-ligated borane with nickel was well exemplified extend chemical space Ni-catalyzed cross-electrophile coupling.

Language: Английский

Citations

7
Photoredox Nickel-Catalyzed Coupling/Controllable Defluorination: Access to α-Fluoroarylacetic Amides and Acetates DOI
Jie Gao,

Pin-Pin Yao,

Xian‐Chen He

et al.

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

Published: March 12, 2025

Herein, an electron donor–acceptor complex (EDA)-enabled photoredox nickel-catalyzed coupling/controllable defluorination domino sequence has been successfully developed, providing efficient route to a series of α-fluoroarylacetic esters and amides. This methodology accommodates diverse array commercially available aryl bromides chlorodifluoroaryl carboxylic acid derivatives as suitable substrates. Preliminary mechanistic investigations suggest that the reaction is initiated by photoinduced EDA-enabled/nickel-catalyzed direct cross-electrophile coupling, with further proceeding through generation EDA complexes, facilitating controllable reductive process.

Language: Английский

Citations

0
Nickel/Photoredox Dual-Catalyzed, Regioselective 1,2-Carboacylation of Alkenes via Synergistic Alkyl and Benzoyl Radical Coupling DOI

Xian‐Chen He,

Jie Gao, Yang Li

et al.

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

Citations

0
Visible Light-Induced, Nickel-Catalyzed Late-Stage 4-Alkylation of Hantzsch Esters with Alkyl Bromide DOI

Yanling Liu,

Xian‐Chen He,

Jie Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10987 - 10997

Published: July 22, 2024

Herein, visible light-induced, nickel-catalyzed direct functionalization of the Hantzsch esters (HEs) with readily accessible alkyl bromides has been successfully achieved by taking advantage HE as reductant and substrate through an aromatization-dearomatization process. In this strategy, single electron reduction reactive Ni(I) species is essential for success late-stage transformation. A wide range 4-alkyl-1,4-dihydropyridines were rapidly assembled in moderate to good yields under mild conditions, rendering photoinduced approach attractive synthetic medicinal chemistry.

Language: Английский

Citations

3
EDA-Enabled Three-Component Polarity-Crossover Cyclization: Modular Installation of Fully Substituted γ-Lactams DOI

Jia-Le Yan,

Zhilin Liu, Kai Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9598 - 9603

Published: Oct. 28, 2024

A photoinduced three-component radical addition-aminalization cascade was accomplished, enabling rapid assembly of a wide range densely functionalized γ-lactams. Key to this transformation is the electron-donor-acceptor (EDA) generation enamine and in situ trapping an iminium intermediate with bromodifluoroacetamide. This rationally designed protocol fully takes advantage polarity crossover (enamine-iminium) process, providing modular previously inaccessible scaffolds. The reaction proceeds under mild conditions excellent regio- diastereoselectivity, which amenable structurally varied substrates pharmaceuticals.

Language: Английский

Citations

1
Thiophene and benzo[b]thiophene DOI

Sean Chin Chan,

Andrii Monastyrskyi

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 89 - 122

Published: Jan. 1, 2024

Language: Английский

Citations

0
Electrochemical formylation of aryl halides by using DMF as formyl source DOI

Congcong Qiang,

Mengyun Wu,

Jingru Han

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An electrochemical protocol for the formylation of aryl halides by using DMF as a formyl source was developed to produce aromatic aldehydes in moderate good yields.

Language: Английский

Citations

0