As part of ongoing efforts in this laboratory to design and synthesize multidentate soft-N-donors as effective complexants for chemoselective minor actinide extraction from used nuclear fuel, a series of aminated mono-1,2,4-triazinylpyridines were required. This study focuses on streamlining convergent access to a diverse array of functionalized N-donors using Pd-catalysis from a common synthon affording access to pyridinyl triazines as the 4,4'-amino derivatives which are commercially limited and unsuccessful in traditional condensation chemistry. A general Pd-catalyzed method for the double amination of functionalized pyridinyl-1,2,4-triazines with low catalyst/ligand loadings enabling the formation of 16 novel complexants is presented.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.5b00710 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A Pd-catalyzed route to carborane-fused boron heterocycles.
Chem Sci
July 2024
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology 130 Meilong Road 200237 Shanghai China
Due to the expanding applications of icosahedral carboranes in medicinal and materials chemistry research, their functionalizations have become one of the central themes in boron-rich cluster chemistry. Although several strategies for incorporating nitrogen-containing nucleophiles on a single boron vertex of the icosahedral carboranes (CBH) have been developed, methods for preparing clusters with vicinal B-N moieties are still lacking. The steric bulk of icosahedral carboranes and disparate electronic and steric nature of the N-containing groups have rendered the vicinal diamination challenging.
View Article and Find Full Text PDFBoosting the Reactivity of Bis-Lactones to Enable Step-Growth Polymerization at Room Temperature.
Macromolecules
April 2024
POLYMAT and Department of Polymers and Advanced Materials/Physics, Chemistry and Technology, University of the Basque Country UPV/EHU, Joxe Mari Korta Center Avda. Tolosa 72, 20018 Donostia-San Sebastian, Spain.
The development of new sustainable polymeric materials endowed with improved performances but minimal environmental impact is a major concern, with polyesters as primary targets. Lactones are key monomers thanks to ring-opening polymerization, but their use in step-growth polymerization has remained scarce and challenging. Herein, we report a powerful bis(γ-lactone) () that was efficiently prepared on a gram scale from malonic acid by Pd-catalyzed cycloisomerization.
View Article and Find Full Text PDFSynthesis, Molecular Packing and Semiconductor Properties of V-Shaped N-Heteroacene Dimers.
Chem Asian J
October 2023
Department of Chemistry, The Chinese University of Hong Kong Shatin, New Territories, Hong Kong, China.
This article presents two groups of V-shaped π-scaffolds that consist of two N-heteroacene units fused with either a rigid or flexible eight-membered ring. These rigid and flexible N-heteroacene dimers were synthesized through the condensation of tetraphenylenetetraone with the corresponding diamine and the Pd-catalyzed cross-coupling of tetrabromodibenzo[a,e]cyclooctatetraene with the corresponding diamine, respectively. A comparison of electronic structures and properties of the two groups of V-shaped N-heteroacene dimers shows subtle difference between the rigid and flexible eight-membered ring linkers in forming extended π-systems.
View Article and Find Full Text PDFRoom-Temperature Cu-Catalyzed Amination of Aryl Bromides Enabled by DFT-Guided Ligand Design.
J Am Chem Soc
March 2023
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, Massachusetts 02139, United States.
Ullmann-type C-N coupling reactions represent an important alternative to well-established Pd-catalyzed approaches due to the differing reactivity and the lower cost of Cu. While the design of anionic Cu ligands, particularly those by Ma, has enabled the coupling of various classes of aryl halides and alkyl amines, most methods require conditions that can limit their utility on complex substrates. Herein, we disclose the development of anionic ,-diarylbenzene-1,2-diamine ligands that promote the Cu-catalyzed amination of aryl bromides under mild conditions.
View Article and Find Full Text PDFPd-Catalyzed Aerobic Intermolecular 1,2-Diamination of Conjugated Dienes: Regio- and Chemoselective Synthesis of Piperazines and 2-Piperazinones.
Chemistry
October 2022
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P. R. China.
Dinitrogen heterocycles are among the most important molecular structures, and the synthesis of these types of structures through intermolecular 1,2-diamination of olefins is a direct and efficient method. However, the types of nitrogen sources are mostly derived from ureas or arylamines, and nitrogen sources from aliphatic amines are still limited due to their distinct electronic and steric effects. Herein, we report a palladium-catalyzed aerobic intermolecular 1,2-diamination of conjugated dienes, using ethanediamine and α-amino amide derivatives as nitrogen sources respectively, for the synthesis of piperazines and 2-piperazinones in good yields (up to 95 %) and with high regio- and chemoselectivities.
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!