A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of C-O and C-C bonds.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol402600r | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Aerobic Copper-Catalyzed Hydroxysulfonylation of Vinylarenes with Sodium Sulfinates.
J Org Chem
January 2025
College of Chemistry and Chemical Engineering, Green Catalysis & Synthesis Key Laboratory of Xinyang City, Xinyang Normal University, Xinyang 464000, China.
A novel and efficient method for the intermolecular hydroxysulfonylation of vinylarenes using sodium sulfinates has been achieved through aerobic copper catalysis. This transformation proceeded smoothly with green air as the terminal oxidant in the presence of Cu (I)/1,10-phenanthroline as an efficient catalytic system, leading to an array of β-hydroxysulfones in moderate to high yields. The significant advantages of this protocol are the mild reaction conditions, readily available starting materials, good functional-group compatibility, synthetic convenience, and practicability.
View Article and Find Full Text PDFModular access to saturated bioisosteres of anilines via photoelectrochemical decarboxylative C(sp)-N coupling.
Nat Commun
January 2025
Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai, 200240, China.
In drug development, the substitution of benzene rings in aniline-based drug candidates with saturated bridged bicyclic ring systems often enhances pharmacokinetic properties while preserving biological activity. However, current efforts predominantly focuses on bicyclo[1.1.
View Article and Find Full Text PDFBiophysiochemically favorable, antithrombotic and pro-endothelial coordination compound nanocoating of copper (II) with protocatechuic acid & nattokinase on flow-diverting stents.
Colloids Surf B Biointerfaces
January 2025
Institute of Biomedical Engineering, College of Medicine, Key Laboratory of Advanced Technologies of Materials, Ministry of Education, Southwest Jiaotong University, Chengdu 610031, China. Electronic address:
Neurovascular flow-diverting stents (FDSs) are revolutionizing the paradigm for treatment of intracranial aneurysms, but they still face great challenges like post- implantation acute thrombosis and delayed reendothelialization. Surface modification is of crucial relevance in addressing such key issues. In this study, we fabricated an ultrathin nanocoating out of copper (II) together with protocatechuic acid (PCA) and nattokinase (NK) bioactive molecules on NiTi FDSs via a coordination chemistry approach, with favorable biophysiochemical interactions, to fulfill this goal.
View Article and Find Full Text PDFCopper catalyzed selective methane oxidation to acetic acid using O.
Chem Sci
January 2025
Department of Chemistry, Indian Institute of Technology Hauz Khas Delhi New Delhi 110016 India
The direct transformation of methane into C oxygenates such as acetic acid selectively using molecular oxygen (O) is a significant challenge due to the chemical inertness of methane, the difficulty of methane C-H bond activation/C-C bond coupling and the thermodynamically favored over-oxidation. In this study, we have successfully developed a porous aluminium metal-organic framework (MOF)-supported single-site mono-copper(ii) hydroxyl catalyst [MIL-53(Al)-Cu(OH)], which is efficient in directly oxidizing methane to acetic acid in water at 175 °C with a remarkable selectivity using only O. This heterogeneous catalyst achieved an exceptional acetic acid productivity of 11 796 mmol mol h in 9.
View Article and Find Full Text PDFAerobic oxidation of alkylarenes and polystyrene waste to benzoic acids a copper-based catalyst.
Chem Sci
January 2025
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University Changchun Jilin 130012 China
The chemical recycling of polystyrene (PS) waste to value-added aromatic compounds is an attractive but formidable challenge due to the inertness of the C-C bonds in the polymer backbone. Here we develop a light-driven, copper-catalyzed protocol to achieve aerobic oxidation of various alkylarenes or real-life PS waste to benzoic acid and oxidized styrene oligomers. The resulting oligomers can be further transformed under heating conditions, thus achieving benzoic acid in up to 65% total yield through an integrated one-pot two-step procedure.
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!