The development of readily tunable and regioselective C-H functionalization reactions that operate solely through catalyst control remains a challenge in modern organic synthesis. Herein, we report that simple silver catalysts supported by common nitrogenated ligands can be used to tune a nitrene transfer reaction between two different types of C-H bonds. The results reported herein represent the first example of ligand-controlled and site-selective silver-promoted C-H amination.
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http://dx.doi.org/10.1021/ja5094309 | DOI Listing |
ACS Catal
December 2024
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
A Rh(III)-catalyzed sequential C-H bond addition to dienes and in situ formed aldimines was developed, allowing for the preparation of otherwise challenging to access amines with quaternary centers at the -position. A broad range of dienes were effective inputs and installed a variety of aryl and alkyl substituents at the quaternary carbon site. Aryl and alkyl sulfonamide and carbamate nitrogen substituents were incorporated by using different formaldimine precursors.
View Article and Find Full Text PDFOrg Lett
December 2024
Division of Medicinal Chemistry, CSIR-Institute of Microbial Technology, Chandigarh 160036, India.
A novel palladium-catalyzed intramolecular C-H amination via oxidative coupling exploiting inactivated N-substituted aryl amines on indoles for the one-pot synthesis of novel 11-benzo[4,5]imidazo[1,2-]indole derivatives is reported. The optimized reaction conditions accommodated a wide range of electronic variations on both the indole and the pendant aryl amine ring, resulting in products with good to excellent yields.
View Article and Find Full Text PDFJ Xenobiot
December 2024
Department of Chemical Engineering, University of Pretoria, Pretoria 0028, South Africa.
The direct discharge of cationic surfactants into environmental matrices has exponentially increased due to their wide application in many products. These compounds and their degraded products disrupt microbial dynamics, hinder plant survival, and affect human health. Therefore, there is an urgent need to develop electroanalytical assessment techniques for their identification, determination, and monitoring.
View Article and Find Full Text PDFInorg Chem
December 2024
Henan Key Laboratory of Polyoxometalate Chemistry, College of Chemistry and Molecular Sciences, Henan University, Kaifeng, Henan 475004, P. R. China.
Amide compounds are widely present in drug molecules and natural products, which can be synthesized by acid-amine condensation. It is urgent to design new photocatalysts for achieving both nitroaromatic reduction and C-H oxidation to obtain raw materials, carboxylic acids, and aromatic amines. Herein, a novel isopolymolybdate-incorporated photoactive metal-organic framework, -TPT, was constructed by combining the oxidation catalyst [MoO], Ni(II) cation, and photosensitive ligand 2,4,6-tri(4-pyridyl)-1,3,5-triazine (TPT).
View Article and Find Full Text PDFInorg Chem
December 2024
Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Facultad de Ciencias, Universidad de Zaragoza - CSIC, 50009 Zaragoza, Spain.
An active catalytic system for the cross-dehydrogenative coupling (CDC) of a wide range of secondary amines with silanes is reported. The iridium(III) derivatives [Ir(H)(X)(κ-NSi)(L)] (NSi = {4,8-dimethylquinoline-2-yloxy}dimethylsilyl; L = coe, X = Cl, ; L = coe, X = OTf, ; L = PCy, X = Cl, ; L = PCy X = OTf, ), which are stabilized by a weak yet noticeable Ir···H-C agostic interaction between the iridium and one of the C-H bonds of the 8-Me substituent of the NSi ligand, have been prepared and fully characterized. These species have proven to be effective catalysts for the CDC of secondary amines with hydrosilanes.
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