Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 5, 2024
A TBADT-photocatalyzed cascade hydrogen atom transfer procedure was established for the synthesis of α-CF 3 -1,4-diketones from aldehydes and 2-bromo-3,3,3-trifluoro-1-propenes.
Language: Английский
Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5074 - 5081
Published: June 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.
Language: Английский
Citations
13
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 4024 - 4040
Published: Jan. 1, 2024
This review provides a comprehensive overview of metal catalysis in photo-electrochemical systems, discussing reaction mechanisms and offering prospects for this triadic catalytic mode.
Language: Английский
Citations
13
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(24)
Published: Feb. 20, 2024
Abstract Herein we describe a sustainable and efficient photocatalytic method for the stereoselective radical alkylation of chiral sulfinyl imines. By employing readily available non‐prefunctionalized precursors cost‐effective TBADT as direct HAT photocatalyst, successfully obtain diverse amines with high yields excellent diastereoselectivity under mild conditions. This provides an approach accessing array medicinally relevant compounds, including both natural synthetic α‐amino acids, aryl ethyl amines, other structural motifs commonly found in approved pharmaceuticals product.
Language: Английский
Citations
12
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(19), P. 3799 - 3842
Published: Jan. 1, 2024
Tetrabutylammonium decatungstate (TBADT) has recently emerged as an intriguing photocatalyst under visible-light or near-visible-light irradiation in a wide range of organic reactions that were previously not conceivable. Given its ability to absorb visible light and excellent effectiveness activating unactivated chemical bonds, it is promising addition traditional photocatalysts. This review covers some the contemporary developments photocatalysis enabled by TBADT catalyst 2023, with contents organized reaction type.
Language: Английский
Citations
11
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(22)
Published: April 16, 2024
Abstract In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources employing TBADT a cost‐effective photocatalyst for direct hydrogen atom transfers (HAT), achieved successful conversion these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields high diastereoselectivity under mild reaction conditions.
Language: Английский
Citations
8
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(68), P. 8946 - 8977
Published: Jan. 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.
Language: Английский
Citations
8
Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)
Published: Nov. 30, 2023
Alkene dicarbofunctionalization is an efficient strategy and operation-economic fashion for introducing complexity in molecules. A nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes the simultaneous construction one C(sp3)-C(sp3) bond C(sp3)-C(sp2) has been developed. The mild catalytic method provided valuable indanethylamine derivatives with wide substrate scope good functional group compatibility. An enantioselective was also achieved pyridine-oxazoline as a ligand. efficiency metallaphotoredox demonstrated concise synthesis pharmaceutically active compounds.
Language: Английский
Citations
16
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 5305 - 5313
Published: March 26, 2024
Over the past few decades, Narasaka–Heck-type difunctionalization of tethered alkenes has emerged as a powerful strategy to produce heterocyclic scaffolds. However, asymmetric synthesis rarely been explored. Herein, we report robust palladium-catalyzed enantioselective Narasaka–Heck cyclization–Sonogashira reaction alkene-tethered oxime esters and terminal alkynes. By employing new Ming-Phos ligand, obtain high yields pyrrolines with quaternary stereocenter enantioselectivities under mild conditions. Density functional theory (DFT) study reveals weak interaction between aromatic ring substrate fragment naphthyl group in which probably accounts for stereoselectivity.
Language: Английский
Citations
5
Chemical Science, Journal Year: 2024, Volume and Issue: 15(20), P. 7502 - 7514
Published: Jan. 1, 2024
The exploitation of new reactive species and novel transformation modes for their synthetic applications have significantly promoted the development organic methodology, drug discovery, advanced functional materials. α-Iminyl radical cations, a class distonic ions, exhibit great potential synthesis valuable molecules. For generation, conjugate addition to α,β-unsaturated iminium ions represents concise yet highly challenging route, because
Language: Английский
Citations
5
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(62)
Published: Aug. 10, 2024
The difunctionalization of alkenes represents a powerful tool to incorporate two functional groups into the alkene bones for increasing molecular complexity and has been widely utilizations in chemical synthesis. Upon catalysis green, sustainable, mild photo-/electrochemistry technologies, much attentions have attracted development new tactics transformations important alkane feedstocks driven by C-H radical functionalization. Herein, we summarize recent advances photo-/electrocatalytic enabled We detailedly discuss substrate scope mechanisms reactions selecting impressive synthetic examples, which are divided four sections based on final terminated step, including oxidative radical-polar crossover coupling, reductive radical-radical transition-metal-catalyzed coupling.
Language: Английский
Citations
5