Photoinduced Copper‐Catalyzed Three‐Component Radical Carboamination of Styrene Derivatives DOI Open Access

Xiao-Die Huan,

Juan Zhang,

Wenjing Xiao

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(23)

Published: Aug. 28, 2024

Abstract The catalytic three‐component radical carboamination of alkenes has recently emerged as an alternative and robust platform for the rapid construction diverse valuable amines. Despite great advances in this field, new methods that enable highly selective access to chemical space surrounding amine functional groups are still high demand. Herein, we report a generally applicable visible light‐induced copper‐catalyzed cyanoalkylamination reaction alkenes, oxime carbonates, benzoyloxycarbamates. This protocol demonstrates chemo‐selectivity, broad substrate scope, good group tolerance, providing variety cyanoalkylated aliphatic amines with yields.

Language: Английский

Recent advances in dual photoredox/nickel catalyzed alkene carbofunctionalised reactions DOI

Anilkumar Kommoju,

Kattamuri Snehita,

K. Sowjanya

et al.

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

9

Solvent-Controlled Silver Catalyzed Radical Transformation of α-Imino-Oxy Acids with Cyclic Aldimines DOI
Jingjing Wang, Yong Qin,

Ke Cui

et al.

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

Published: Jan. 1, 2025

A silver-catalyzed cross coupling of cyclic aldimines and α-imino-oxy acids has been developed. The solvent-dependent reaction could selectively deliver either imine moiety retained nitriles or ring-opened oxonitriles in moderate yields.

Language: Английский

Citations

1

Visible-Light-Induced photoredox aerobic coupling of sulfonium ylides and amines leading to E-selective formation of 2-amino-2-butene-1,4-diones DOI

Ning Xian,

Xiaochen Ji, Guo‐Jun Deng

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel visible-light-induced photoredox three-component aerobic coupling reaction of sulfoxonium ylides and amines is reported.

Language: Английский

Citations

0

Photoinduced, Copper-Catalyzed Enantioconvergent Synthesis of β-Aminoalcohol Derivatives DOI
Arup Mondal, Gregory C. Fu

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

In view of the frequent occurrence carbon-nitrogen bonds in organic compounds, development powerful new methods for construction such is expected to greatly impact many fields that utilize molecules. While substitution an alkyl electrophile by a nitrogen nucleophile seemingly straightforward approach generating bond, practice classical pathways have very substantial limitations case unactivated secondary and tertiary electrophiles. Recent reports transition metals can catalyze certain reactions electrophiles are therefore considerable significance; however, virtually no been developed wherein absolute stereochemistry controlled together with bond formation. Herein, we address this dual challenge reactivity enantioselectivity, describing photoinduced, copper-catalyzed enantioconvergent synthesis β-aminoalcohol derivatives via coupling anilines racemic, β-haloethers. We apply method catalytic asymmetric metolachlor, report array mechanistic studies consistent reaction pathway propose.

Language: Английский

Citations

0

Cyclic Diphenylchloronium-Salt-Triggered Coupling of Sulfides with Nucleophiles: Modular Assembly of Pharmaceuticals DOI

Bangxiong Kang,

Wei Li, Huanfeng Jiang

et al.

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

Published: April 2, 2025

We report a novel coupling strategy enabled by cyclic diphenylchloronium salt that facilitates reactions between sulfides and diverse nucleophiles, including oxygen- nitrogen-based species. The methodology efficiently produces structurally varied valuable compounds, carbamates, carboxylic esters, aryl ethers, alkylated amines, under mild, operationally simple conditions. protocol's synthetic utility was highlighted through modular preparation of five important drugs structural analogues, demonstrating significant potential for drug discovery applications.

Language: Английский

Citations

0

Photocatalytic Oxidative C(sp3)-H/N–H Cross-Dehydrogenative Coupling of Tertiary Anilines with Amides/Imides: Synthesis of N-Mannich Bases DOI

Qiaerbati Adelibieke,

Bulunuer Yusan,

Xiong Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

A photocatalytic method for the synthesis of N-Mannich bases has been developed through C(sp3)-H/N-H cross-dehydrogenative coupling N,N-dimethylanilines with amides/imides. This process utilizes 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) as photocatalyst and is conducted at ambient temperature atmospheric air. Various aromatic, heteroaromatic aliphatic (cyclic) amides, well imides were successfully employed, yielding moderate to good results. Preliminary mechanistic isotope-labeling studies indicate that reaction likely proceeds via a single electron transfer pathway involves an α-aminoalkyl radical intermediate.

Language: Английский

Citations

0

Visible‐Light Mediated Nickel‐Catalyzed Asymmetric Difunctionalizations of Alkenes DOI Open Access

Han‐Tong Zhao,

Jia‐Ni Lin,

Wei Shu

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(67)

Published: Aug. 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.

Language: Английский

Citations

3

Biomimetic Dehydrogenative Intermolecular Formal Allylic Amidation of Branched α‐Olefins DOI Creative Commons
Xiaoyang Fu,

Jiarui Tian,

Mingjun Zhang

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 12(2)

Published: Nov. 18, 2024

Abstract Allylic amide moieties are commonly encountered in natural products and privileged structures pharmaceuticals agrochemicals. Moreover, because allylic can be to converted into an array of high‐value motifs, they have been widely employed organic synthesis. However, the development catalytic systems for intermolecular amidation olefins, particularly branched α ‐olefins, has proven challenging. Here, a biomimetic, synergistic method is reported that combines photoredox, cobalt, Brønsted base catalysis synthesis substituted amides from ‐olefins simple imides without using oxidants. This low‐cost, operationally features broad substrate scope excellent functional group compatibility. it successfully used functionalization several structurally complex molecules demonstrating method's potential utility medicinal chemistry applications. Mechanistic studies revealed C( sp 3 )─N bond formation mediated by nitrogen‐centered radical intermediate, which generated via sequence involving deprotonation single‐electron oxidation.

Language: Английский

Citations

3

Construction of extremely low-symmetry double-stranded helicates based on terpyridine ligands with consecutive unsymmetrical modification DOI

Shaozhi Wang,

Jianjun Ma, Ning Zhang

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 17, 2025

Language: Английский

Citations

0

Regioselective 1,4-Hydroamination of 1,3-Dienes by Photoredox/Cobalt Dual Catalysis DOI

Pei-Ting Li,

Quansheng Mou, Wei Yu

et al.

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

Published: Feb. 14, 2025

Herein, we report a visible-light-driven and cobalt-mediated 1,4-hydroamination reaction of 1,3-dienes with arylmines as the nucleophiles. The involves regioselective addition [CoIII]–H to 1,3-diene, followed by oxidation nucleophilic substitution amines. Using Ir(ppy)3 photocatalyst enables cobalt redox cycle be implemented without using an external oxidant hydride regent. This protocol can applied well forge carbon–oxygen carbon–sulfur bonds in analogous way.

Language: Английский

Citations

0