Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
A convenient protocol for the synthesis of selenated benzoxepine derivatives via iron(III)-catalyzed 7-endo-trig cyclization has been first established via reaction of 1,7-diene containing nonactivated allyl and dialkyl diselenides under room temperature and air conditions. Research has shown that different dialkyl diselenides could react with a wide range of 1,7-diene to achieve seven-membered products in good to excellent yields. Furthermore, this synthesis was directed to obtain the desired target products, indicating that this approach has an excellent chemical selectivity. With this novel strategy, various benzoxepines bearing different seleno groups could be obtained, making this protocol more efficient and of practical value.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.5c01611 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Selenification/Cyclization Reactions of Nonactivated Allyl 1,7-Diene: Access to Seleno-Benzo[]oxepine Derivatives.
J Org Chem
September 2025
Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, PR China.
A convenient protocol for the synthesis of selenated benzoxepine derivatives via iron(III)-catalyzed 7-endo-trig cyclization has been first established via reaction of 1,7-diene containing nonactivated allyl and dialkyl diselenides under room temperature and air conditions. Research has shown that different dialkyl diselenides could react with a wide range of 1,7-diene to achieve seven-membered products in good to excellent yields. Furthermore, this synthesis was directed to obtain the desired target products, indicating that this approach has an excellent chemical selectivity.
View Article and Find Full Text PDFTitanium cis-DACH Salan Catalyst for the Efficient Epoxidation of Nonactivated Olefins with Hydrogen Peroxide-Terminal-Selective Epoxidation of Multiply Unsaturated Terpenes.
Chemistry
July 2025
Department of Chemistry, Organic Chemistry, University of Cologne, Greinstraße 4, D-50939, Cologne, Germany.
We report a new generation of highly active and readily available homogeneous titanium catalysts for the epoxidation of nonactivated olefins with aqueous hydrogen peroxide. Key feature is the introduction of pentafluorophenyl substituents into a salan ligand derived from cis-1,2-diaminocyclohexane (cis-DACH). Our novel salan ligand is accessible in one single step by reductive alkylation of cis-DACH with 3-(pentafluorophenyl)salicylic aldehyde.
View Article and Find Full Text PDFAsymmetric Relay Catalysis Enables Unreactive Allylic Alcohols to Participate in 1,3-Dipolar Cycloaddition of Azomethine Ylides.
J Am Chem Soc
February 2025
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Current synthetic transformations occur readily with starting materials that possess both innate reactivity and steric accessibility or functional-group-oriented reactivity. However, achieving reactions with inactive feedstock substrates remains significantly challenging and normally requires cumbersome prior functional group manipulations. Herein, we report an unprecedented example of catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with nonactivated alkenes enabled by copper/ruthenium relay catalysis.
View Article and Find Full Text PDFChemoselective Adsorption of Allyl Ethers on Si(001): How the Interaction between Two Functional Groups Controls the Reactivity and Final Products of a Surface Reaction.
J Phys Chem Lett
July 2024
Institut für Angewandte Physik and Zentrum für Materialforschung, Justus-Liebig-Universität Giessen, Heinrich-Buff-Ring 16, D-35392 Giessen, Germany.
Selective adsorption of multifunctional molecules is rarely observed when the different functional groups react via nonactivated reaction channels. Although the latter is also the case for ether cleavage and the adsorption of C=C double bonds on the highly reactive Si(001) surface, we find that allyl ethers, which combine both functional groups, react on Si(001) selectively via the cleavage of the molecules' ether group. In addition, our XPS measurements at 90, 150, and 300 K indicate an increased reactivity of the ether group when compared to monofunctional ethers.
View Article and Find Full Text PDFRadical-Dearomative Generation of Cyclohexadienyl Pd(II) toward the 3D Transformation of Nonactivated Phenyl Rings.
Adv Sci (Weinh)
March 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology (SCUT), Guangzhou, 510640, China.
Traditional palladium-catalyzed dearomatization of (hetero)arenes takes place via an ionic pathway and usually requires elevated temperatures to overcome the energy barrier of the dearomative insertion step. Herein, a combination of the radical and two-electron pathways is disclosed, which enables room temperature dearomative 3D transformations of nonactivated phenyl rings with Pd(0) as the catalyst. Experimental results together with density functional theory (DFT) calculations indicate a versatile π-allyl Pd(II) species, cyclohexadienyl Pd(II), possibly is involved in the dearomatization.
View Article and Find Full Text PDF