Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4264 - 4268

Опубликована: Янв. 1, 2024

Herein, we describe an electrochemical strategy that enables the aminotrideuteromethylthiolation of isocyanides with anilines and CD 3 SSO Na, providing unprecedented route to access S -CD isothioureas in satisfactory yields.

Язык: Английский

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Aminothiolation of alkenes with azoles and Bunte salts

Frontiers in Chemistry, Год журнала: 2024, Номер 11

Опубликована: Янв. 22, 2024

We have developed an intermolecular aminothiolation of simple olefins using Bunte salt as a thiolating agent. This protocol produces thiyl free radicals under PIDA oxidation conditions, eliminating the need for transition-metal catalysts. The method has wide range substrate applicability and is suitable large-scale preparation late-stage modification drug molecules.

Язык: Английский

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Metal-free three-component amino- and carbotrideuteromethylthiolation of alkenes in water

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(21), С. 6064 - 6068

Опубликована: Янв. 1, 2024

Three-component amino- and carbotrideuteromethylthiolation of alkenes in water.

Язык: Английский

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I₂‐Promoted Alkylsulfenylation/Cyclization of Enaminones with S‐Alkyl Bunte Salts: Synthesis of 3‐Alkylsulfenylated Chromones

ChemistrySelect, Год журнала: 2025, Номер 10(5)

Опубликована: Фев. 1, 2025

Abstract A novel protocol for effective and efficient synthesis of 3‐alkylsulfenylated chromones in moderate to good yields via I 2 ‐promoted alkylsulfenylation/cyclization enaminones with S ‐alkyl Bunte salts has been described. This reaction features a broad substrate scope, functional group tolerance, metal‐ oxidant‐free conditions.

Язык: Английский

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Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Язык: Английский

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Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)

Опубликована: Июль 17, 2024

1,2-Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N-functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2-diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N-heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2-aminothiolation styrenes.

Язык: Английский

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Enhancing Electrocatalytic Semihydrogenation of Alkynes via Weakening Alkene Adsorption over Electron-Depleted Cu Nanowires

ACS Nanoscience Au, Год журнала: 2024, Номер 4(5), С. 349 - 359

Опубликована: Авг. 8, 2024

Electrochemical semihydrogenation (ESH) of alkynes to alkenes is an appealing technique for producing pharmaceutical precursors and polymer monomers, while also preventing catalyst poisoning by alkyne impurities. Cu recognized as a cost-effective highly selective ESH, whereas its activity somewhat limited. Here, from mechanistic standpoint, we hypothesize that electron-deficient can enhance ESH promoting the rate-determining step alkene desorption. We test this hypothesis utilizing Cu-Ag hybrids electrocatalysts, developed through welding process Ag nanoparticles with nanowires. Our findings reveal these rationally engineered exhibit notable enhancement (2-4 times greater) in conversion rates compared isolated NPs or NWs, maintaining over 99% selectivity products. Through combination operando computational studies, verify electron-depleted sites, resulting electron transfer between nanowires, effectively weaken adsorption alkenes, thereby substantially boosting activity. This work not only provides insights into but stimulates compelling strategies involving hybridizing distinct metals optimize

Язык: Английский

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LiOtBu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde N-Tosylhydrazones Approach to 3-Substituted 1H-Dibenzo[e,g]indazoles

Molecules, Год журнала: 2023, Номер 28(24), С. 8061 - 8061

Опубликована: Дек. 13, 2023

A two-step, one-pot synthesis of 3-substituted 1H-dibenzo[e,g]indazoles in good to high yields via a LiOtBu-promoted intramolecular 1,3-dipolar cyclization 2'-alkynyl-biaryl-2-aldehyde N-tosylhydrazones was developed. The N-Ts-hydrazones used were prepared situ the reactions 2'-alkynyl-biaryl-2-aldehydes and TsNHNH2(p-methylbenzenesulfonohydrazide). Two types signals related hydrogen bonds, forming several products, observed 1H NMR spectra recorded DMSO-d6, assigned N-H bonds their dimeric species product tautomer.

Язык: Английский

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Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH₂ Group Alongside Unprotected Amines

Angewandte Chemie, Год журнала: 2024, Номер 136(45)

Опубликована: Июль 17, 2024

Abstract 1,2‐Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N‐functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2‐diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N ‐heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2‐aminothiolation styrenes.

Язык: Английский

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Silver-Catalyzed 1,2-Thiosulfonylation of Alkenes: Development of a Nucleophilic d₃-Methylthiolating Reagent

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 25, 2024

Development of robust

Язык: Английский

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