Chemoselective reduction of imines and azobenzenes catalyzed by silver N-heterocyclic carbene complexes

Han, Bo; Jiao, Hongmei; Chen, Rong; Zhang, Yuqi; Wang, Ji‐Jiang

doi:10.1039/d3qo00003f

Cited by 5 publications

(2 citation statements)

References 43 publications

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“…1 H NMR and 13 C NMR spectra were consistent with the literature. 21 4-((2-Phenylhydrazineylidene)methyl)phenol (3d). Two solutions were fed by peristaltic pumps; solution A was a solution of 1a (13.10 g, 107.3 mmol) diluted up to 50 mL with EtOH in a measuring flask (2.146 mmol/mL), and solution B was a solution of 2c (12.45 g, 115.1 mmol) diluted up to 25 mL with EtOH in a measuring flask (4.605 mmol/mL).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Application of Taylor Vortex Flow Reactor Enabling Precise Control of Nucleation in Reactive Crystallization

Hosoya,

Manaka,

Kawajiri

et al. 2024

Org. Process Res. Dev.

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A system that requires slurry handling such as reactive crystallization is not usually compatible with continuous flow synthesis due to the risk of clogging. Here we suggest the use of a Taylor vortex flow reactor to achieve a robust process for imination with reactive crystallization under continuous flow conditions. A Taylor vortex flow reactor realizes high shear stress and mixing efficiency, which accelerate the timing for nucleation of target imines. This effect enabled precise control of nucleation in reactive crystallization and successfully showed the mitigation of significant adhesion to the flow reactor through a long-run experiment for 120 min. This work gives one of the practical strategies to remove the limitation of slurry handling that is not suitable for continuous flow synthesis and increase the performance of flow chemistry.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…13 C NMR (100 MHz, CDCl 3 ): δ 157.70, 148.89, 139.61 (q, J = 1.5 Hz), 136.74, 132.71 (q, J = 32.8 Hz), 130.01, 128.98, 125.82 (q, J = 3.7 Hz), 124.08 (q, J = 270.5 Hz), 121.02, 21.16. 1 H NMR and 13 C NMR spectra were consistent with the literature …”

Section: Methodsmentioning

confidence: 99%

Application of Taylor Vortex Flow Reactor Enabling Precise Control of Nucleation in Reactive Crystallization

Hosoya,

Manaka,

Kawajiri

et al. 2024

Org. Process Res. Dev.

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Tandem Hydrogen‐Borrowing Dehydrogenative Coupling and Hydrodefluorination

Sidhu,

Mondal,

Herbert

2024

Adv Synth Catal

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Dehydrogenative coupling (DC) is an attractive approach to constructing new C‐N bonds using alcohols as electrophiles. In ‘hydrogen‐borrowing’ variants of DC, the H2 liberated can be used to re‐hydrogenate unsaturated intermediates to produce saturated products. Here, we show how so‐generated H2 can also be used to replace fluorine atoms with hydrogens in CF3 groups in a tandem dehydrogenative coupling/hydrodefluorination process.

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A chemoselective and one‐pot method for the synthesis of unsymmetrical secondary amines via coupling reaction of ammonia and aryl(alkyl) halides catalyzed by MNP@IAH@Cu‐IL as a bifunctional nanocatalyst

Nosratollahi,

Soleiman‐Beigi,

Norouzi

2024

Applied Organom Chemis

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Copper, an abundant metal on Earth, has re‐emerged as a suitable alternative to versatile Palladium‐catalyzed C–N coupling. Herein, a new recoverable and reusable bifunctional catalyst was synthesized by combining an ionic liquid and linking Cu(II) on the surface of Fe3O4 nanoparticles. New nanocatalyst (MNP@IAH@Cu‐IL) was completely characterized using different techniques. Continuing, MNP@IAH@Cu‐IL was applied in the synthesis of primary and secondary amines via C(sp2)‐N coupling reaction successfully. This catalyst worked well in the synthesis of anilines derivatives in high yields and excellent quality. Further, we described a novel and one‐pot process for the synthesis of unsymmetrical secondary amine derivatives from two different aryl(alkyl) halides. This procedure shows attractive features such as 100% atom economy, high yields of the desired products under base‐free conditions, excellent functional group tolerance, work‐up simplicity, and recyclability.

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Chemoselective reduction of imines and azobenzenes catalyzed by silver N-heterocyclic carbene complexes

Abstract: Here, the first example of the NHC (N-heterocyclic carbenes) ligand-promoted reduction of imines and azobenzenes with homogeneous silver catalyst is reported. The PhSiH3 induced hydrogenation of imines and azobenzenes and...

Cited by 5 publications

References 43 publications

Application of Taylor Vortex Flow Reactor Enabling Precise Control of Nucleation in Reactive Crystallization

Application of Taylor Vortex Flow Reactor Enabling Precise Control of Nucleation in Reactive Crystallization

Tandem Hydrogen‐Borrowing Dehydrogenative Coupling and Hydrodefluorination

A chemoselective and one‐pot method for the synthesis of unsymmetrical secondary amines via coupling reaction of ammonia and aryl(alkyl) halides catalyzed by MNP@IAH@Cu‐IL as a bifunctional nanocatalyst

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