AI Article Synopsis
- This study introduces a novel three-component carboarylation reaction that combines unactivated imines, arynes, and carbon nucleophiles using 2-(trimethylsilyl)aryl triflates.
- The reaction creates a range of functionalized tertiary amines without the need for transition metals, making it a more straightforward approach.
- Various carbon nucleophiles can be utilized in this reaction, including chloroform, acetonitrile, and methyl propiolate.
Article Abstract
With 2-(trimethylsilyl)aryl triflates as aryne precursors, an unprecedented three-component carboarylation reaction of unactivated imines with arynes and carbon nucleophiles has been developed to access a variety of functionalized tertiary amines under transition metal-free conditions. Suitable carbon nucleophiles include chloroform, acetonitrile, and methyl propiolate.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c6cc09311f | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Stereodivergent Construction of 3,3'-Disubstituted Oxindoles via One-Pot Sequential Allylation/Alkylation and Its Application to the Total Synthesis of Trigolute B and D.
J Am Chem Soc
January 2025
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important and desirable to construct all possible stereoisomers of a lead candidate or a given bioactive natural compound. Synergistic dual catalysis has been recognized as a reliable synthetic strategy for a variety of predictable stereodivergent transformations.
View Article and Find Full Text PDFData Checking of Asymmetric Catalysis Literature Using a Graph Neural Network Approach.
Molecules
January 2025
GSK Carbon Neutral Laboratories for Sustainable Chemistry, Jubilee Campus, University of Nottingham, Triumph Road, Nottingham NG7 2TU, UK.
The range of chemical databases available has dramatically increased in recent years, but the reliability and quality of their data are often negatively affected by human-error fidelity. The size of chemical databases can make manual data curation/checking of such sets time consuming; thus, automated tools to help this process are highly desirable. Herein, we propose the use of Graph Neural Networks (GNNs) to identifying potential stereochemical misassignments in the primary asymmetric catalysis literature.
View Article and Find Full Text PDFA Robust -Symmetric Aluminate Hydride for CO Hydroboration Catalysis: Mechanistic Insights and Countercation Influence on Catalytic Performance.
Inorg Chem
January 2025
Institute of Chemistry, Université de Strasbourg, CNRS, Strasbourg 67000, France.
The present study details the synthesis and characterization of a robust, monomeric Al-H aluminate supported by a tridentate -phenolate ligand, isolated as [][Li(THF)] and [][N(Bu)] salts, which were then exploited as CO hydroboration catalysts. As initial reactivity studies, it was observed that the nucleophilic Al-H anion in [][C] (C = countercation [Li(THF)] or [N(Bu)]) reacts fast with CO, to afford the corresponding Al-formate complexes [][C], which were isolated and structurally characterized. Such anions were then exploited as potential CO reduction catalysts.
View Article and Find Full Text PDFReactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.
Acc Chem Res
January 2025
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.
View Article and Find Full Text PDFSynthesis of benzouracils and carbamates from chloroacetamides through carbon-carbon bond cleavage.
Org Biomol Chem
January 2025
Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman.
This work introduces a mild reaction-condition approach for the direct C-C bond cleavage of amides, resulting in the formation of benzouracil and carbamate structures. This method leverages a C-C bond cleavage strategy that enables nucleophilic addition to the amide carbonyl, involving a reactive spiro intermediate. A diverse range of chloroacetamides were synthesized and utilized as bifunctional starting materials in this transformation.
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!