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

et al.

Published: March 12, 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 non-activated 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

Mechanochemical Iron‐Catalyzed Nitrene Transfer Reactions: Direct Synthesis of N‐Acyl Sulfonimidamides from Sulfinamides and Dioxazolones DOI Creative Commons

Shulei Pan,

Florian F. Mulks, Peng Wu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(5)

Published: Dec. 7, 2023

A mechanochemical synthesis of sulfonimidamides by iron(II)-catalyzed exogenous ligand-free N-acyl nitrene transfer to sulfinamides is reported. The one-step method tolerates a wide range with various substituents under solvent-free ambient conditions. Compared its solution-phase counterpart, this approach shows better conversion and chemoselectivity. Mechanistic investigations ESI-MS revealed the generation crucial iron intermediates.

Language: Английский

Citations

9

Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology DOI Creative Commons

Cairong Wang,

Yan Zhang, Kai Sun

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(4), P. 1998 - 1998

Published: Feb. 20, 2023

Dichalcogenides (disulfides and diselenides), as reactants for organic transformations, are important widely used because of their potential to react with nucleophiles, electrophilic reagents, radical precursors. In recent years, in combination photochemical technology, the application dichalcogenides stable reagents has opened up a new route synthesis various sulfur- selenium-containing compounds. this paper, synthetic strategies disulfides diselenides applications technology reviewed: (i) Cyclization alkenes alkynes; (ii) direct selenylation/sulfuration C−H/C−C/C−N bonds; (iii) visible-light-enabled seleno- sulfur-bifunctionalization alkenes/alkynes; (iv) Direct construction C(sp)–S bond. addition, scopes, limitations, mechanisms some reactions also described.

Language: Английский

Citations

8

Construction of alkynyl and acyl disulfides directly through thiol-modification withN-alkynylthio phthalimides under acid catalysis DOI

Yao-Nan Xue,

Kai Feng,

Jun Tian

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(8), P. 2070 - 2074

Published: Jan. 1, 2023

Acid-catalyzed disulfuration and rearrangement have been disclosed for the construction of alkynyl or acyl disulfides from thiols N -alkynylthio phthalimides, enabling access to disulfide-modified thiodrugs, thiopeptides thioglycosides.

Language: Английский

Citations

7

Rapid Formation of Intramolecular Disulfide Bridges using Light: An Efficient Method to Control the Conformation and Function of Bioactive Peptides DOI
Feng He, Yu Chai,

Zizhen Zeng

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(41), P. 22639 - 22648

Published: Oct. 3, 2023

Disulfide bonds are widely found in natural peptides and play a pivotal role stabilizing their secondary structures, which highly associated with biological functions. Herein, we introduce light-mediated strategy to effectively control the formation of disulfides. Our is based on 2-nitroveratryl (oNv), used photolabile motif, serves both as photocaging group an oxidant (after photolysis). We demonstrated that irradiation oNv-caged thiols UV light could release free rapidly oxidized by locally released byproduct nitrosoarene, leading "break-to-bond" fashion. This highlighted situ restoration antimicrobial peptide tachyplesin I (TPI) from its external disulfide-caged analogue TPI-1. TPI-1 exhibits distorted structure diminished function. However, upon irradiation, β-hairpin membrane activity TPI were largely restored via rapid intramolecular disulfide formation. study proposes powerful method regulate conformation function spatiotemporal manner, has significant potential for design disulfide-centered light-responsive systems.

Language: Английский

Citations

7

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

et al.

Published: March 12, 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 non-activated 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

Citations

2