Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 89 - 122
Published: Jan. 1, 2024
Language: Английский
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
2
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
8
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
4
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
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
ACS Omega, Journal Year: 2025, Volume and Issue: 10(20), P. 20497 - 20508
Published: May 14, 2025
This study presents a practical, efficient, and scalable approach for the C-H formylation of indoles their derivatives using alkyl orthoesters as formylating agents. Boron trifluoride diethyl etherate (BF3·OEt2) was found to be an effective stoichiometric catalyst, with trimethyl orthoformate (TMOF) acting reliable formyl source. method enables rapid efficient synthesis wide range C-formylindoles, including C3, C2, C6, C7 derivatives, well electron-rich aromatic carbaldehydes. Key advantages protocol include its operational simplicity, use inexpensive readily available reagents, neat conditions, ambient reaction temperatures, short times (typically 1-5 min), broad substrate tolerance, scalability. These features make highly versatile suitable diverse synthetic applications.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: May 21, 2025
1,8-Naphthylene dithiocarbonates enable the safe and light-controlled release of carbon monoxide gas (CO). The disulfide byproducts, produced upon blue-light irradiation dithiocarbonates, were readily recovered recycled by reduction reaction with 1,1-carbonyldiimidazole (CDI). photochemical process was investigated 1H NMR, GC, FTIR, UV-vis, DFT calculations. ex situ evolution CO from this recyclable platform applied to a range Pd-catalyzed carbonylative cross-coupling reactions using two-chamber glass apparatus.
Language: Английский
Citations
0
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
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
Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 89 - 122
Published: Jan. 1, 2024
Language: Английский
Citations
0