The selective synthesis of different products from a substrate employing a single catalyst by altering the reaction conditions is challenging. Herein, easy-to-synthesize and cheap CuO NPs catalyzed chemodivergent transfer hydrogenation (TH) of azoarenes to hydrazoarene and aniline derivatives using ammonia borane (AB) under mild condition is disclosed. The practical applicability of the protocol was demonstrated by gram-scale synthesis of hydrazo and aniline derivatives as well as by the reduction of few commercially used dyes such as methyl red, sudan I, sudan III and solvent yellow 7. Several control experiment and deuterium labelling experiments were performed to understand the reaction mechanism. Moreover, the catalyst can be recycled up to six times without considerable loss of catalytic activity.
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http://dx.doi.org/10.1002/chem.202404196 | DOI Listing |
Chemistry
March 2025
Indian Institute of Technology Kanpur, Chemistry, Department of Chemistry, 208016, Kanpur, INDIA.
The selective synthesis of different products from a substrate employing a single catalyst by altering the reaction conditions is challenging. Herein, easy-to-synthesize and cheap CuO NPs catalyzed chemodivergent transfer hydrogenation (TH) of azoarenes to hydrazoarene and aniline derivatives using ammonia borane (AB) under mild condition is disclosed. The practical applicability of the protocol was demonstrated by gram-scale synthesis of hydrazo and aniline derivatives as well as by the reduction of few commercially used dyes such as methyl red, sudan I, sudan III and solvent yellow 7.
View Article and Find Full Text PDFJ Am Chem Soc
March 2025
College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, P. R. China.
Electrochemical nitroarene reduction enables the green production of anilines at ambient conditions thanks to the manipulated transfer of multiple electrons and protons via controlling potentials and currents, but challenges remain in pH-neutral electrolysis using nonprecious catalysts. Here, Chevrel phase MoS with high conductivity and insertable frameworks is proposed for the first time as a cost-efficient candidate with prominent performance and, more importantly, as a new platform to unravel cation effects on nitroarene electroreduction. Nanosized MoS derived from polymer-confined sulfidation affords a high yield (∼95%) and Faradaic efficiency (∼99%) for reducing 4-nitrostyrene to 4-aminostyrene at -0.
View Article and Find Full Text PDFChem Asian J
March 2025
Universidad de Zaragoza, Quimica Inorganica, Pedro Cerbuna s/n, 50009, Zaragoza, SPAIN.
The iridium(I) complexes [IrBr(cod)(κC-tBuImCH2PyCH2NRR')] (NRR' = NEt2, NHtBu) have been prepared by reaction of the corresponding functionalized imidazolium salt with the appropriate dinuclear compound [Ir(µ-OR)(cod)]2 (R = OMe, OEt). These compounds react with H2(g) (5 bar) to afford the pincer iridium(III) dihydrido complexes [IrBrH2(κ3C,N,N'-tBuImCH2PyCH2NRR')] in good yields. The complexes [IrBr(cod)(κC-tBuImCH2PyCH2NRR')] efficiently catalyzed the β-alkylation of a series of secondary alcohols and the N-alkylation of a range of aniline derivatives with primary alcohols, with good selectivities for the β-alkylated alcohol and monoalkylated secondary amine products, respectively, at low catalyst loading, typically 0.
View Article and Find Full Text PDFJ Nat Prod
March 2025
School of Medicine, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China.
The first total synthesis of (±)-talaroenamine B was achieved through a concise four-step procedure. The key feature of this synthetic strategy lies in a one-pot reaction involving I (III)-mediated oxidative dearomatization to construct a racemic cyclohexanedione unit, followed by imination using a chiral auxiliary to afford a separable mixture of diastereoisomers. A further acid-catalyzed substitution reaction of aniline with the diastereoisomers led to the natural product (-)-talaroenamine B and its enantiomer (+)-talaroenamine B.
View Article and Find Full Text PDFJ Colloid Interface Sci
March 2025
Shenzhen Key Laboratory of Polymer Science and Technology, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, China.
Developing cost-effective and high-performance n-type thermoelectric (TE) materials is a significant challenge for their utilization in organic electronics. Clarifying the influence of molecular structure on TE properties is of utmost importance. In this work, the analysis on how the shape and polarity of organic molecules affect the thermoelectric performance of n-type composites based on single-walled carbon nanotubes (SWCNTs) is presented.
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