Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4722 - 4729
Published: Jan. 1, 2024
The concurrent reduction of α-trifluoromethyl alkyl bromides and the cross-coupling THF with heterocycles in one pot have been realized through synergetic action a halogen bond Ni catalysis.
Language: Английский
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(5), P. 3725 - 3732
Published: Feb. 21, 2024
The chiral allylic sulfonylated group is a unique structural motif embedded in range of natural products and pharmaceuticals. Notably, the synthesis structurally diverse derivatives via alkylsulfonylation 1,3-dienes remains underexplored because its inherent challenges stereocontrol regioselectivity. Herein, photoinduced, palladium-catalyzed enantioselective 1,2-alkylsulfonylation conjugated described. A wide variety alkyl bromides, 1,3-dienes, sodium sulfinates could be facilely coupled to generate value-added with high enantioselectivity. Finally, utility this difunctionalization protocol was demonstrated pharmaceutical analogue synthesis.
Language: Английский
Citations
19
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(31)
Published: March 28, 2024
Abstract Photoinduced aryl radical generation is a powerful strategy in organic synthesis that facilitates the formation of diverse carbon‐carbon and carbon‐heteroatom bonds. The synthetic applications photoinduced complex compounds, including natural products, physiologically significant molecules, functional materials, have received immense attention. An overview current developments production methods their uses given this article. A generalized idea how to choose reagents approach for radicals described, along with techniques associated mechanistic insights. Overall, article offers critical assessment results as well selection reaction parameters specific context cascades, cross‐coupling reactions, functionalization, selective C−H functionalization substrates.
Language: Английский
Citations
15
Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1478 - 1482
Published: Feb. 9, 2024
Herein, a dual photoredox/nickel catalyzed formylation of aryl bromide with commercially available 2,2-dimethoxy-N,N-dimethylethan-1-amine as an effective CO source has been successfully achieved, delivering series aromatic aldehydes in moderate to good yields. Compared the traditional reductive carbonylation process, this newly designed synthetic protocol provides straightforward toolbox access aldehydes, obviating use carbon monoxide and stoichiometric reductants. Finally, utility direct reaction was demonstrated pharmaceutical analogue synthesis.
Language: Английский
Citations
7
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
Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7716 - 7720
Published: Oct. 16, 2023
Herein, a direct cross-dehydrogenative C-H amination of indoles has been successfully achieved, enabled by the merger photocatalysis with nickel catalysis. This developed process does not require stoichiometric oxidants and prefunctionalization amine partners, providing concise platform for C-N bond formation. Moreover, synthetic practicality this transformation was well revealed its high step- atom-economy, reaction efficiency, broad functional group tolerance.
Language: Английский
Citations
11
Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 18, 2025
Comprehensive Summary We have developed a series of 1‐methylpyridine‐2(1 H )‐thione (MPT) analogues to be used as organocatalysts. The MPT catalysts are easily prepared and bench‐stable. In our previous work, we found that the ground‐state catalyst could act nucleophile generate primary radicals via an S N 2 pathway. However, this reaction was limited benzyl radicals. Herein, reported new catalytic property catalyst. photoexcited ( E (MPT ·+ /MPT*) = –1.60 V vs. Ag/AgCl in MeCN) reduce NHPI esters through single electron transfer process. Various carbon radicals, including radical, well primary, secondary tertiary alkyl generated easily. Notably, amino acids, peptide, pharmaceuticals, other biologically active molecules modified by using methodology showing potential synthetic utility method.
Language: Английский
Citations
0
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
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
Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
We present a photoredox nickel-catalyzed intermolecular cyclization between N -arylacrylamides and readily accessible alkyl bromides, which affords diverse range of 3,3-disubstituted oxindoles in moderate to high yields.
Language: Английский
Citations
0