Synthesis of N–H Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids as Aminating Agent DOI
Yi Huang, Shiyang Zhu, Gang He

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6263 - 6273

Published: April 23, 2024

Herein, we presented a practical methodology for the intermolecular aziridination of alkenes, using HOSA as aminating agent, alongside pyridine or piperidine base, within HFIP solvent system. Notably, this approach showcases excellent reactivity, especially with nonactivated and facilitates transformation various alkenes substrates, including mono-, di-, tri, tetra-substituted into aziridines moderate to yield. This method presents promising avenue synthesizing from wide range featuring benefits straightforward operation, mild reaction conditions, extensive substrate compatibility, scalability.

Language: Английский

Generation of perthiyl radicals for the synthesis of unsymmetric disulfides DOI Creative Commons

Fei Zhou,

X. He, Mi Zhou

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 2, 2025

Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside a single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously. Here, authors novel transition-metalfree

Language: Английский

Citations

0
Nanozymes with Modulable Inhibition Transfer Pathways for Thiol and Cell Identification DOI
Lijun Hu, Lei Jiao, Chengjie Chen

et al.

Analytical Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

The elementary mechanism and site studies of nanozyme-based inhibition reactions are ambiguous urgently require advanced nanozymes as mediators to elucidate the effect. To this end, we develop a class featuring single Cu–N catalytic configurations B–O sites binding on porous nitrogen-doped carbon substrate (B6/CuSA) for inducing modulable transfer at atomic level. full redistribution electrons across sites, induced by incorporation, yields B6/CuSA with enhanced peroxidase-like activity versus CuSA. More importantly, CuSA features in cysteine expresses competitive through coordination bonds, an constant 0.048 mM. Benefiting from way nanozymes, possesses mixed approaches noncovalent bonds delivers record-mixed interaction 0.054 mM noncompetitive 0.71 Based CuSA, multichannel sensor array accomplishes detection various cancer cells, normal thiols. design principle work is endowed guidelines preliminary evaluation massive potential thiols, cell discrimination, disease prediction.

Language: Английский

Citations

0
Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations DOI Creative Commons

Seungmin Lee,

Minsuk Kim,

Hyewon Han

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 200 - 216

Published: Jan. 22, 2025

Over the past decade, dioxazolones have been widely used as N -acylamide sources in amidation processes of challenging substrates, typically employing precious transition metals. However, these catalytic systems often present several challenges associated with cost, toxicity, stability, and recyclability. Among 3d metals, copper catalysts gaining increasing attention owing to their abundance, cost-effectiveness, sustainability. Recently, applied chemical transformation dioxazolones, conferring a convenient protocol towards amidated products. This review highlights recent advancements synthetic transformations particular examples salts.

Language: Английский

Citations

0
Regioselective N-arylation of N-Acylsulfenamides Enabled by o-Quinone Diimides DOI
Xuebin Yan, Rui Zhao, Yu‐Hang Miao

et al.

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

Published: Feb. 27, 2025

The functionalization of N-acylsulfenamides is a research focus in organosulfur chemistry, as the N-S array has unique properties and versatile applications. Although great progress been made S-functionalization, N-functionalization, especially N-arylation N-acylsulfenamides, rarely explored because lower nucleophilicity N-site. Herein, we report Brønsted acid-catalyzed regioselective reaction with o-quinone diimides. Under mild metal-free conditions, wide range N-arylated have prepared good yields excellent regioselectivity. ease gram-scale synthesis transformations into useful sulfonamides demonstrates their synthetic practicality.

Language: Английский

Citations

0
Nitrene-mediated Aminative N–N–N Coupling: Facile Access to Triazene 1-Oxides DOI Creative Commons
Shiyang Zhu, Hai-Ruo Zhang,

Boyang Sun

et al.

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

Published: Jan. 1, 2025

A nitrene-mediated aminative N–N–N coupling enables direct triazene 1-oxide synthesis via an aminonitrene–nitrosoarene pathway.

Language: Английский

Citations

0
Mechanochemical syntheses of N-acyl sulfinamidines via iron-nitrenoids and their conversions to sulfur(VI) derivatives DOI Creative Commons

Shulei Pan,

Peng Wu, Yijie Hu

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0
Synthesis of N-Acylsulfenamides from Amides and N-Thiosuccinimides DOI

Jessica T Liu,

Daniel S. Brandes, Nathaniel S. Greenwood

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 55(15), P. 2353 - 2360

Published: Dec. 20, 2022

Abstract Herein is reported a robust and general method for the preparation of N-acylsulfenamides, important functionalities that have recently been utilized as central inputs asymmetric synthesis high oxidation state sulfur compounds. This straightforward transformation proceeds by reaction primary amides, carbamates, sulfonamides, sulfinamides, ureas with stable N-thiosuccinimides or N-thiophthalimides, which in turn are prepared single step from commercial thiols. The use N-thiosuccinimide N-thiophthalimide reactants desirable because it obviates highly reactive sulfenyl chlorides.

Language: Английский

Citations

17
Access to disulfides through ligand-controlled nickel-catalyzed dithiosulfonate and alkyl halides DOI
Wang Chen, Xinyu Liu,

Daopeng Sheng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 830 - 835

Published: Dec. 19, 2023

Nickel-catalyzed C–SS reductive cross-coupling reaction of dithiosulfonate and unactivated alkyl halides for producing unsymmetric disulfides with broad substrate scope under mild conditions excellent functional group tolerance.

Language: Английский

Citations

10
Polysulfide synthesisviavisible-light-induced heteroarene-migratory dithiosulfonylation reaction DOI
Baoxu Wang,

Zijing Hu,

Lu Huang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(47), P. 7247 - 7250

Published: Jan. 1, 2023

A visible-light-induced radical cascade heteroarene-migratory dithiosulfonylation has been developed to synthesize polysulfides, which can be transformed into dihydrothiophene and homoallyl disulfide derivatives.

Language: Английский

Citations

9
Visible-light-induced iron-catalyzed S–N cross-coupling of thiols with dioxazolones DOI
Jingjing Tang, Ning Yan, Yiwei Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7529 - 7533

Published: Jan. 1, 2023

The visible-light-promoted iron-catalyzed S–N cross coupling of thiols with dioxazolones is described. This reaction occurred via an exogenous-photosensitizer-free process and showed wide substrate scope under mild conditions.

Language: Английский

Citations

9