Catalytic selective annulation of 2-azirines constitutes a general and modular strategy for the generation of molecular complexity. By using Pd-catalyzed ring opening/heterocyclization associated with direct cleavage of C-N and C-C bonds under appropriate conditions, the formation of imidazoles is presented. Alternatively, the silver-catalyzed radical [3 + 2] cycloannulation of 2-azirines and 1,3-dicarbonyl compounds provides highly functionalized pyrrole derivatives. Both aliphatic cyclic and acyclic diketones are tolerated with good regioselectivity. Moreover, a radical capture experiment was carried out to determine the proposed mechanism, providing support for a facile radical process.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.3c00430 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Metal-Controlled Switchable Regioselective Synthesis of Substituted Imidazoles and Pyrroles Ring Opening/Cyclocondensation with 2-Azirines.
J Org Chem
July 2023
College of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, China.
Catalytic selective annulation of 2-azirines constitutes a general and modular strategy for the generation of molecular complexity. By using Pd-catalyzed ring opening/heterocyclization associated with direct cleavage of C-N and C-C bonds under appropriate conditions, the formation of imidazoles is presented. Alternatively, the silver-catalyzed radical [3 + 2] cycloannulation of 2-azirines and 1,3-dicarbonyl compounds provides highly functionalized pyrrole derivatives.
View Article and Find Full Text PDFTransition Metal-Controlled Divergent Annulations of Azomethine Imines with Iodonium Ylides -Centered [1,2]-Rearrangement.
Org Lett
April 2023
Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450052, P. R. China.
Transition metal-controlled divergent annulation reactions of azomethine imines with iodonium ylides -centered [1,2]-rearrangement have been developed. The azomethine imino group, as a switchable and transient directing group (DG), underwent intramolecular nucleophilic addition and generated bicyclic diaziridine, which facilitated the -centered [1,2]-rearrangement and subsequent divergent annulations in the presence of different metal complexes as the catalysts. The benzo[]chromen-1-one and pyrano[]isochromene scaffolds could be independently constructed with Rh(III) and Ru(II), respectively.
View Article and Find Full Text PDFTunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity.
Org Lett
March 2023
National Engineering Research Center for Carbohydrate Synthesis, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, People's Republic of China.
The three-component reactions of enaminones, α-diazo esters/ketones, and -butyl nitrite (TBN) for the switchable synthesis of isomeric isoxazoles have been realized. The catalysis with Cu(II) salt provides 3,4-disubsituted isoxazoles via [3 + 2] cycloaddition. On the other hand, the catalysis of Ag(I) with identical substrates leads to isomeric isoxazoles with reversed C3 and C4 substitution based on a key [2 + 1] cycloaddition.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!