Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Дек. 10, 2024
An enantioselective Pd/Cu-catalyzed sequential Heck/Sonogashira reaction of electron-rich enamides is reported, providing various 3-propargyl isoindolinone derivatives bearing quaternary stereogenic centers in good yield and enantioselectivity.
Язык: Английский
Organic Letters, Год журнала: 2024, Номер 26(24), С. 5074 - 5081
Опубликована: Июнь 10, 2024
The nickel/photoredox dual catalysis system is an efficient conversion platform for the difunctionalization of unsaturated hydrocarbons. Herein, we disclose first nickel/photoredox-catalyzed intramolecular 1,2-arylsulfonylation allenes, which can accurately construct a C(sp2)–C(sp2) bond and C(sp3)–S bond. reaction exhibits excellent chemoselectivity regioselectivity, allowing modular conformations diverse series 3-sulfonylmethylbenzofuran derivatives. Control experiments showed that bipyridine ligand crucial formation stable σ-alkyl nickel intermediate, providing possibility sulfonyl radical insertion. Meanwhile, electrophilic facilitates further oxidative addition intermediate inhibits with allenes. In addition, control experiments, cyclic voltammetry tests, Stern–Volmer density functional theory calculations afford evidence Ni(0)/Ni(I)/Ni(II)/Ni(III) pathway in this 1,2-arylsulfonylation.
Язык: Английский
Процитировано
13
Chemical Communications, Год журнала: 2024, Номер 60(68), С. 8946 - 8977
Опубликована: Янв. 1, 2024
Alkene carbofunctionalization reactions have great potential for synthesizing complex molecules and constructing structures in natural products medicinal chemistry. Recently, dual photoredox/nickel catalysis has emerged as a novel strategy alkene carbofunctionalization. Nickel offers numerous advantages over other transition metals, such cost-effectiveness, abundance, low toxicity, moreover, it many oxidation states. catalysts exhibit excellent catalytic activity photoredox/transition metal catalysis, facilitating the formation of carbon-carbon or carbon-heteroatom bonds organic transformations. This review highlights latest advancements photoredox/nickel-catalyzed carbofunctionalizations includes literature published from 2020 to 2024.
Язык: Английский
Процитировано
8
Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown
Опубликована: Июль 27, 2024
Abstract Radical‐involved arylative cross‐coupling reactions have recently emerged as an attractive strategy to access valuable aryl‐substituted motifs. However, there still exist several challenges such limited scope of radical precursors/acceptors, and lack general asymmetric catalytic systems, especially regarding the multicomponent variants. Herein, we reported a copper‐Box system for three‐component vinylarenes 1,3‐enynes, with oxime carbonates aryl boronic acids. The proceed under practical conditions in absence or presence visible‐light irradiation, affording chiral 1,1‐diarylalkanes, benzylic alkynes allenes good enantioselectivities. Mechanistic studies imply that copper/Box complexes play dual role both generation ensuing cross‐coupling. In cases irradiation could improve activity complex toward initial generation, enabling better efficiency match between formation
Язык: Английский
Процитировано
4
Dalton Transactions, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
The DFT calculation explains the mechanism of forming 5- exo and 6- endo cyclization products in Ni-catalyzed reductive arylalkylation alkenes.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Март 25, 2025
A ligand-modulated synergetic nickel/photoredox-catalyzed exo-arylalkylation of unactivated alkynes was developed that strikingly different from the known endo-arylalkylation activated arylacetylenes. The unique arylalkylation pathway due to formation a π-allyl-Ni complex alkyne where nickel species engaged in distinctive dual-catalytic cycle. exo-alkenylation applied divergent synthesis tryptamines and benzofurylethylamines.
Язык: Английский
Процитировано
0
Опубликована: Июнь 12, 2024
Radical-involved arylative cross-coupling reactions have recently emerged as an attractive strategy to access valuable aryl-substituted motifs. However, there still exist several challenges such limited scope of radi-cal precursors/acceptors, and lack general asymmetric catalytic systems, especially regarding the multicom-ponent variants. Herein, we reported a copper-Box system for three-component vinylarenes 1,3-enynes, with oxime carbonates aryl boronic acids. The proceed under practical conditions in absence or presence visible-light irradiation, affording chiral 1,1-diarylalkanes, benzylic alkynes allenes good enantioselectivities. Mechanistic studies imply that copper/Box complexes play dual role both radical generation ensuing cross-coupling. In cases irradiation could improve activity complex toward initial generation, enabling better efficiency match between formation
Язык: Английский
Процитировано
3
Organic Letters, Год журнала: 2024, Номер 26(26), С. 5560 - 5565
Опубликована: Июнь 25, 2024
An intermolecular nickel-catalyzed reductive 1,2-alkylarylation of acrylates with cyclopropylamine NHP esters and aryl iodides is reported. This operationally simple protocol provides direct access to 1-alkylcyclopropylamine scaffolds. The mild conditions are compatible four-membered α-amino strained rings as well five- six-membered ring systems. products undergo cyclization α-arylated spirocyclic γ-lactams─a motif present in several pharmaceuticals.
Язык: Английский
Процитировано
2
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1484 - 1489
Опубликована: Янв. 1, 2024
Herein, we report a copper-catalyzed alkylarylation reaction of alkenes using N -fluoroamides and arylboronic acids.
Язык: Английский
Процитировано
1
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3058 - 3065
Опубликована: Янв. 1, 2024
A novel and general nickel/photoredox dual catalysis platform for benzyl alcohol C–O bond activation/Csp 2 –Csp 3 cross coupling of benzothiazolyl bromide free alcohol, enabled by the catalytic generation an alkyl radical, is reported.
Язык: Английский
Процитировано
1
Chemistry - A European Journal, Год журнала: 2024, Номер 30(67)
Опубликована: Авг. 13, 2024
Abstract Difunctionalizations of alkenes represent one the most straightforward protocols to build molecular complexity due simultaneous construction two vicinal bonds cross π‐bond alkenes. It is extremely attractive yet challenging control stereochemistry outcome this event. Over past years, visible‐light and Ni‐catalyzed asymmetric difunctionalizations provide an environmental benign promising solution for saturated carbon centers with regio‐ enantioselectivity. In Concept, initiative progress enantioselective enabled by nickel catalysis has been summarized. Moreover, further efforts directions development mediated discussed.
Язык: Английский
Процитировано
1