Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η(6)-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jacs.6b00386 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Isoxazoles to Multisubstituted Thiazoles via an Ammonium Iodide-Catalyzed Formal [3+2] Cycloaddition Reaction.
Org Lett
September 2025
National Key Laboratory of Advanced Drug Delivery and Release Systems, School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, P. R. China.
A method for the conversion of isoxazoles into thiazoles by skeleton rearrangement has been achieved by an ammonium iodide-catalyzed cycloaddition protocol under mild conditions with a broad substrate scope and good functional group tolerance. Most appealingly, the reaction can proceed smoothly without the addition of any transition metal catalyst. Detailed mechanistic studies, including control experiments and key reaction intermediate characterization, reveal an intermolecular [3+2] cycloaddition reaction pathway.
View Article and Find Full Text PDFRuthenium-Catalyzed Intermolecular [2 + 2] Cycloaddition of Unactivated Allenes and Alkynes with Unusual Regioselectivity.
J Am Chem Soc
September 2025
Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.
Described here is an efficient protocol for intermolecular [2 + 2] cycloaddition of unactivated and unsymmetrical allenes and alkynes with unusual regioselectivity, counterintuitively favoring the most hindered isomer. CpRu(MeCN)PF served as a uniquely effective catalyst, providing diverse 3-alkylidenecyclobutenes with a broad scope and good functional group compatibility. Both experiments and DFT studies provided important insights into the mechanism, particularly the unusual regioselectivity.
View Article and Find Full Text PDFA dual-engineered covalent organic framework with charge-oxygen synergy promotes photocatalytic dipolar [3 + 2] cycloaddition.
Chem Sci
August 2025
College of Chemistry and Materials Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, Institute of Life Science and Green Development Hebei University Baoding Hebei 071002 P. R. China
The photocatalytic oxidative dipolar [3 + 2] cycloaddition reaction is a promising green approach for producing pyrrolo[2,1-]isoquinolines. However, developing sustainable cycloaddition methods with heterogeneous photocatalysts is still in its infancy, largely owing to their low reactivity and photostability. Herein, we propose a charge-oxygen synergy strategy through a dual-engineered covalent organic framework (COF) by integrating π-spacers with donor-acceptor motifs to promote intermolecular cycloaddition.
View Article and Find Full Text PDFMechanistic insights into the (3 + 2) cycloaddition of azomethine ylide with dimethyl acetylenedicarboxylate bond evolution theory.
RSC Adv
August 2025
Laboratory of Applied Physics, Department of Physics, Faculty of Sciences of Sfax, University of Sfax Sfax Tunisia.
The mechanistic pathway of the (3 + 2) cycloaddition (32CA) between azomethine ylide 1 and dimethyl acetylenedicarboxylate 2, affording 4-isoxazoline derivatives, was elucidated Density Functional Theory (DFT) calculations employing the B3LYP-D3 functional and the 6-311++G(d,p) basis set in 1,4-dioxane. Reactivity insights derived from Conceptual DFT (CDFT) demonstrated that compound 1 behaves as an ambiphilic species with significant nucleophilic and electrophilic tendencies, whereas compound 2 functions predominantly as an electrophile. These electronic features reveal a marked polarity in the cycloaddition and align with a forward electron density flux (FEDF) governing the reaction process.
View Article and Find Full Text PDFAchieving controllable packing mode and broad colour-tunable emission the end group effect in pyrene-based aggregation-induced emission luminogens.
Chem Sci
August 2025
School of Science and Engineering, Shenzhen Institute of Aggregate Science and Technology, The Chinese University of Hong Kong Shenzhen Guangdong 518172 P. R. China
To clarify the impact of the end groups on aggregation behaviour and emission properties, a series of α-cyanostilbene pyrene-based compounds (Py-R and Py-PR) were synthesized. These compounds display aggregation-induced emission characteristics with broad colour-tunable solid-state emission with the colour ranging from cyan to deep red (500-667 nm), achieved by modulating their end groups. The electronic effect of these end groups plays a key role in regulating the emission and the aggregation mode, demonstrating a strong correlation with Hammett constants.
View Article and Find Full Text PDF