Potassium Carbonate Catalyzed Intramolecular Post-Ugi Hydroamination Reaction Leading to N-Aryl Piperazine Derivatives DOI
Mohammad Hosein Sayahi, Mohammad Mahdavi,

Rozita Yazzaf

и другие.

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Апрель 14, 2025

Abstract N-Arylpiperazines are prominent structures found in natural products and synthetic chemical entities, including therapeutic agents. In this work, we introduce a novel strategy for the effective synthesis of distinctive piperazine compounds through post-Ugi cyclization under transition-metal-free conditions. This method involves formation four-component Ugi adduct by combining an aldehyde, isocyanide, primary propargylamine, oxamic acid. Subsequently, intramolecular alkyne hydroamination reaction occurs, leading to derivative carbon–nitrogen bond formation. The have been characterized 1H 13C NMR spectroscopy.

Язык: Английский

Cobalt-catalyzed synthesis of amides from alkenes and amines promoted by light DOI
Mason S. Faculak, Alexander M. Veatch, Erik J. Alexanian

и другие.

Science, Год журнала: 2024, Номер 383(6678), С. 77 - 81

Опубликована: Янв. 4, 2024

Catalytic methods to couple alkene and amine feedstocks are valuable in synthetic chemistry. The direct carbonylative coupling of alkenes amines holds promise as a perfectly atom-economical approach amide synthesis, but general remain underdeveloped. Herein, we report an hydroaminocarbonylation catalyzed by unmodified, inexpensive cobalt carbonyl under mild conditions low pressure promoted light. Silane addition after the reaction enables sequential cobalt-catalyzed reduction, constituting formal hydroaminomethylation. These exhibit exceptional scope across both components with high chemo- regioselectivity proceed efficiently even absence solvent. formation hydridocobalt through photodissociation ligand is proposed enable catalytic activity conditions, which addresses long-standing challenge catalysis.

Язык: Английский

Процитировано

25

Aminoalkylation of Alkenes Enabled by Triple Radical Sorting DOI
William L. Lyon, Johnny Wang, Jesús Alcázar

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

The direct synthesis of C(sp3)-rich architectures is a driving force for innovation in synthetic organic chemistry. Such scaffolds impart beneficial properties onto drug molecules that correlate with greater clinical success. Consequently, there strong impetus to develop new methods by which access sp3-rich from commercial feedstocks, such as alkenes. Herein, we report three-component aminoalkylation reaction utilizes the principles triple radical sorting regioselectively add N-centered and C-centered radicals across This process relies upon photoredox catalysis transform alkyl bromides reductively activated precursors into high-energy species redox-neutral fashion. A broad scope coupling partners demonstrated, multiple applications, including facile syntheses pharmacophoric substituted N-heterocycles.

Язык: Английский

Процитировано

5

Nickel-Catalyzed Asymmetric Homobenzylic Hydroamidation of Aryl Alkenes to Access Chiral β-Arylamides DOI
Xiang Lyu,

Eunmi Jeon,

Changhyeon Seo

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Фев. 25, 2025

Herein, we introduce a Ni-catalyzed asymmetric homobenzylic hydroamidation reaction that efficiently addresses the dual challenges of achieving regio- and enantioselectivity in synthesis β-(hetero)arylethylamides. By employing transposed NiH catalysis approach, this method facilitates formation key chiral nickel-amido intermediates, enabling insertion into alkenes to produce desired β-arylamide products with excellent enantioselectivity. The exhibits high functional group tolerance utilizes readily available starting materials vinylarenes react dioxazolone as robust amidating source. Notably, approach was successfully applied pharmaceutical compounds natural products, such Clobenzorex, Direx, Selegiline, Sacubitril, Cipargamin.

Язык: Английский

Процитировано

3

Recent advances in C(sp3)–N bond formation via metallaphoto-redox catalysis DOI
Juan Zhang,

Xiao-Die Huan,

Xin Wang

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(50), С. 6340 - 6361

Опубликована: Янв. 1, 2024

In this review, the state-of-the-art advances in radical-involved C(sp 3 )–N bond formation via metallaphotoredox catalysis have been highlighted, which are organized according to different catalytic modes, reaction types, and substrate classes.

Язык: Английский

Процитировано

14

Emergence of a distinct mechanism of C–N bond formation in photoenzymes DOI
Felix C. Raps,

Ariadna Rivas-Souchet,

Chey M. Jones

и другие.

Nature, Год журнала: 2024, Номер unknown

Опубликована: Окт. 8, 2024

Язык: Английский

Процитировано

12

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization DOI
Zhengyang Chen, Dan Xiong, Nengzhong Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2762 - 2767

Опубликована: Янв. 1, 2024

A P(NMe2)3-catalyzed [4 + 2] annulation of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization has been developed.

Язык: Английский

Процитировано

10

Photocatalytic Anti-Markovnikov Hydroamination of Alkenes with Primary Heteroaryl Amines DOI
Eric P. Geunes, Jonathan M. Meinhardt, Emily J. Wu

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(40), С. 21738 - 21744

Опубликована: Окт. 3, 2023

We report a light-driven method for the intermolecular anti-Markovnikov hydroamination of alkenes with primary heteroaryl amines. In this protocol, electron transfer between an amine substrate and excited-state iridium photocatalyst affords aminium radical cation (ARC) intermediate that undergoes C–N bond formation nucleophilic alkene. Integral to reaction success is electronic character amine, wherein increasingly electron-deficient amines generate reactive ARCs. Counteranion-dependent reactivity observed, triflate photocatalysts are employed in place conventional hexafluorophosphate complexes. This exhibits broad functional group tolerance across 55 examples N-alkylated products derived from pharmaceutically relevant

Язык: Английский

Процитировано

24

Organic Synthesis Away from Equilibrium: Contrathermodynamic Transformations Enabled by Excited-State Electron Transfer DOI
A. T. Lin, Sumin Lee, Robert R. Knowles

и другие.

Accounts of Chemical Research, Год журнала: 2024, Номер 57(13), С. 1827 - 1838

Опубликована: Июнь 21, 2024

ConspectusChemists have long been inspired by biological photosynthesis, wherein a series of excited-state electron transfer (ET) events facilitate the conversion low energy starting materials such as H

Язык: Английский

Процитировано

7

MXenes as Heterogeneous Thermal Catalysts: Regioselective Anti-Markovnikov Hydroamination of Terminal Alkynes with 102 h–1 Turnover Frequencies DOI
Rubén Ramírez‐Grau, Pablo García-Aznar, Germán Sastre

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Янв. 20, 2025

Due to their conductive properties and optoelectronic tunability, MXenes have revolutionized the area of electrocatalysis active materials in supercapacitors. In comparison, there are only a few reports on as thermal catalysts for general organic reactions. Herein, unprecedented catalytic activity Ti3C2 MXene hydroamination alkynes is reported, overcoming limitations poor activity, lack selectivity, stability, which generally encountered solid known so far. case Ti3C2, exhibits almost complete selectivity anti-Markovnikov regioisomer, both aliphatic amines less-reactive aromatic amines. also efficiently catalyzes intramolecular hydroamination, leading formation indol heterocycles. The C-C multiple bonds reaction with atom efficiency that may form C-N from convenient reagents. maximum number sites nanosheets quantified by thermoprogrammed NH3 desorption. measured TOF values order 102 h-1, highest value being 350 h-1 1-hexyne n-butylamine. Therefore, among heterogeneous studied, its per site comparable best reported Density functional theory calculations models indicate cooperation neighboring Ti atoms mechanism. Considering compositional structural versatility MXenes, present findings open door further application other

Язык: Английский

Процитировано

1

Iridium‐Catalyzed Remote Site‐Switchable Hydroarylation of Alkenes Controlled by Ligands DOI
Fei Li, Yicong Luo,

Jinbao Ren

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(41)

Опубликована: Авг. 23, 2023

An iridium-catalyzed remote site-switchable hydroarylation of alkenes was reported, delivering the products functionalized at subterminal methylene and terminal methyl positions on an alkyl chain controlled by two different ligands, respectively, in good yields with to excellent site-selectivities. The catalytic system showed functional group tolerance a broad substrate scope, including unactivated activated alkenes. More importantly, regioconvergent transformations mixtures isomeric were also successfully realized. results mechanistic studies demonstrate that reaction undergoes chain-walking process give [Ar-Ir-H] complex alkene. subsequent processes proceed through modified Chalk-Harrod-type mechanism via migratory insertion alkene into Ir-C bond followed C-H reductive elimination afford hydrofunctionalization site-selectively.

Язык: Английский

Процитировано

14