Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.
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http://dx.doi.org/10.1021/jacs.9b02266 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Nankai University, SKLEOC, 300071, Tianjin, CHINA.
Amino groups are abundant in both natural and synthetic molecules, offering highly accessible sites for modifying native biorelevant molecules. Despite significant progress with more reactive thiol groups, methods for connecting two amino groups with reversible linkers for bioconjugation applications remain elusive. Herein, we report the use of oxidative decarboxylative condensation of glyoxylic acid to crosslink two alkyl amines via a compact formamidine linkage, applicable in both intra- and intermolecular contexts.
View Article and Find Full Text PDFBiochim Biophys Acta Bioenerg
January 2025
CNC-Center for Neuroscience and Cell Biology, University of Coimbra, Coimbra, Portugal; CIBB - Centre for Innovative Biomedicine and Biotechnology, University of Coimbra, Coimbra, Portugal.
Mitochondrial dysfunction and increased reactive oxygen species (ROS) generation play an import role in different human pathologies. In this context, mitochondrial targeting of potentially protective antioxidants by their coupling to the lipophilic triphenylphosphonium cation (TPP) is widely applied. Employing a six‑carbon (C) linker, we recently demonstrated that mitochondria-targeted phenolic antioxidants derived from gallic acid (AntiOxBEN) and caffeic acid (AntiOxCIN) counterbalance oxidative stress in primary human skin fibroblasts by activating ROS-protective mechanisms.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Secció de Química Inorgànica, Departament de Química Inorgànica i Orgànica, Universitat de Barcelona, Martí i Franquès 1-11, 08028, Barcelona, Spain.
The preparation of organochalcogens has increased in recent times due to their promising biological activity properties. This work studies the reaction mechanism of a nickel(0)-catalyzed cross-coupling between benzonitrile and propanethiol to produce new C-S bonds by computational means. The proposed mechanism follows the classical oxidative addition/transmetalation/reductive elimination cross-coupling sequence, involving an unusual oxidative addition of a Ph-CN bond onto the active species.
View Article and Find Full Text PDFMol Pharm
January 2025
Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China.
Developing low-toxicity, high-efficacy, and fast-acting strategies to manage acute liver injury (ALI) is critical due to its rapid progression and potential for severe outcomes. Curcumin (CUR) has shown promise in ALI therapy due to its ability to modulate the inflammatory microenvironment by scavenging reactive oxygen species (ROS). Nevertheless, CUR is highly hydrophobic limiting its bioavailability and effective in vivo transport, which hinders its further application.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
IISER Kolkata: Indian Institute of Science Education and Research Kolkata, Department of Chemical Sciences, Mohanpur, 741246, Nadia, INDIA.
Chiral allyl amines are important structural components in natural products, pharmaceuticals, and chiral catalysts. Herein, we report a cobalt-catalyzed enantioselective reductive coupling of imines with internal alkynes to synthesize chiral allyl amines. The reaction is catalyzed by a cobalt complex derived from commercially available bisphosphine ligand utilizing zinc as the electron donor.
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