AI Article Synopsis
- Mixed benzofuranyl carbonates, made from chiral chloroformates, can rearrange when nucleophilic catalysts are present, leading to C-carboxylated benzofurans with different degrees of stereochemical differentiation (dr).
- Using chiral nucleophilic catalysts showed some improvement in the dr, but the best outcomes were achieved by fine-tuning the auxiliary and catalyst used in the reaction.
- For instance, compound 8k was produced with an impressive 9:1 dr, demonstrating the effectiveness of the optimization strategies.
Article Abstract
Mixed benzofuranyl carbonates derived from chiral chloroformates rearranged in the presence of nucleophilic catalysts to give C-carboxylated benzofurans with variable dr. The use of chiral nucleophilic catalysts gave modest improvement in dr, but better results were obtained by optimizing auxiliary and catalyst. Thus, 8k was obtained with 9:1 dr.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo7021444 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Dearomative Addition-Hydrogen Autotransfer for Branch-Selective -Heteroaryl C-H Functionalization via Ruthenium-Catalyzed C-C Couplings of Diene Pronucleophiles.
J Am Chem Soc
January 2025
Department of Chemistry, University of Texas at Austin, Austin 78712, Texas, United States.
A novel mechanism for -heteroaryl C-H functionalization via dearomative addition-hydrogen autotransfer is described. Upon exposure to the catalyst derived from RuHCl(CO)(PPh) and Xantphos, dienes - suffer hydroruthenation to form allylruthenium nucleophiles that engage in -heteroaryl addition-β-hydride elimination to furnish branched products of C-C coupling - and -. Oxidative cleavage of isoprene adducts , , , and followed by ruthenium-catalyzed dynamic kinetic asymmetric ketone reduction provides enantiomerically enriched -heteroarylethyl alcohols - and, therefrom, -heteroarylethyl amines -.
View Article and Find Full Text PDFSite-Selective Copper(I)-Catalyzed Hydrogenation of Amides.
J Am Chem Soc
January 2025
Institut für Chemie, Technische Universität Chemnitz, Straße der Nationen 62, 09111 Chemnitz, Germany.
We present a bifunctional catalyst consisting of a copper(I)/N-heterocyclic carbene and an organocatalytic guanidine moiety that enables, for the first time, a copper(I)-catalyzed reduction of amides with H as the terminal reducing agent. The guanidine allows for reactivity tuning of the originally weakly nucleophilic copper(I) hydrides - formed in situ - to be able to react with difficult-to-reduce amides. Additionally, the guanidine moiety is key for the selective recognition of "privileged" amides based on simple and readily available heterocycles in the presence of other amides within one molecule, giving rise to hitherto unknown site-selective catalytic amide hydrogenation.
View Article and Find Full Text PDFUnlocking the Nucleophilic Functionalization Potential of a Natural Asphalt: Grafting a Pd(0)-Diethanolamine Complex as a Recyclable Catalyst for Upgrading Biaryl Synthesis.
Langmuir
January 2025
Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran.
Article Synopsis
- This study presents a new method for upgrading natural asphalt into a catalyst through a process called metal-free sonobromination.
- The method involves creating a palladium complex on natural asphalt, which is then used as a recoverable catalyst in the Suzuki reaction for synthesizing biphenyl derivatives.
- The process is environmentally friendly, uses a green solvent, and showcases the potential for sustainable materials development from renewable resources.
HPO promoted reactions of thioamides with 2-substituted benzyl alcohols.
Org Biomol Chem
January 2025
Department of Chemistry, University of Calcutta, 92, A. P. C. Road, Kolkata - 700 009, West Bengal, India.
In this study, we have investigated the reactivity of thioamides with alcohols by utilizing HPO as a low-toxicity, cost-effective Brønsted acid catalyst. This report includes a methodology for the synthesis of thioesters from thioamides and 2-hydroxyaryl alcohols. Thioesters are emerging as a notable class of organic molecules due to their biological relevance, extensive use in drug discovery, and industrial applications.
View Article and Find Full Text PDFCatalytic Enantioselective Nucleophilic Amination of α-Halo Carbonyl Compounds with Free Amines.
J Am Chem Soc
December 2024
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.
Catalytic enantioselective substitution of the readily available racemic α-halo carbonyl compounds by nitrogen nucleophiles represents one of the most convenient and direct approaches to access enantioenriched α-amino carbonyl compounds. Distinct from the two available strategies involving radicals and enolate ions, herein we have developed a new protocol featuring an electronically opposite way to weaken/cleave the carbon-halogen bond. A suitable chiral anion-based catalyst enables effective asymmetric control over the key positively charged intermediates.
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!