Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Hu, Zenan; Ai, Yongjian; Liu, Lei; Zhou, Junjie; Zhang, Gang; Liu, Hongqi; Liu, Xiangyu; Liu, Zhibo; Hu, Jianshe; Sun, Hongbin; Liang, Qionglin

doi:10.1002/adsc.201801611

Cited by 20 publications

(5 citation statements)

References 54 publications

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“…1 H NMR (400 MHz, CDCl 3 ): δ 7.10 (t, J = 7.8 Hz, 1H), 6.81 (d, J = 7.6 Hz, 1H), 6.72 (s, 1H), 6.66–6.56 (m, 2H), 5.69 (d, J = 17.4 Hz, 1H), 5.19 (d, J = 11.0 Hz, 1H), 3.63 (s, 2H); 13 C{ 1 H} NMR (101 MHz, CDCl 3 ): δ 146.7, 138.8, 137.1, 129.5, 117.0, 114.9, 113.7, 112.8. The NMR data were consistent with reported data …”

Section: Experimental Sectionsupporting

confidence: 91%

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Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

et al. 2022

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In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4′-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

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Section: Experimental Sectionsupporting

confidence: 91%

“…The NMR data were consistent with reported data. 24 2-Aminostyrene (2b). Purified by column chromatography using hexane/EtOAc = 5:1 as eluent.…”

Section: ■ Conclusionmentioning

confidence: 99%

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

et al. 2022

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“…As presented in Fig. 2 a, the peaks centered at 21.2°, 33.2°, 36.6° and 53.2 o corresponding to the (110), (130), (111) and (221) can be indexed to the orthogonal phase of α-FeOOH, respectively (Huang et al 2020 ; Hu et al 2019 ). As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

A comparative study of iron nanoflower and nanocube in terms of antibacterial properties

et al. 2023

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It is known that heavy metal containing nanomaterials can easily prevent the formation of microbial cultures. The emergence of new generation epidemic diseases in the last 2 years has increased the importance of both personal and environmental hygiene. For this reason, in addition to preventing the spread of diseases, studies on alternative disinfectant substances are also carried out. In this study, the antibacterial activity of nanoflower and nanocube, which are easily synthesized and nanoparticle species containing iron, were compared. The antioxidant abilities of new synthesized NF@FeO(OH) and NC@α-Fe 2 O 3 were tested by DPPH scavenging activity assay. The highest DPPH inhibition was achieved with NC@α-Fe 2 O 3 as 71.30% at 200 mg/L. NF@FeO(OH) and NC@α-Fe 2 O 3 demonstrated excellent DNA cleavage ability. The antimicrobial capabilities of NF@FeO(OH) and NC@α-Fe 2 O 3 were analyzed with micro dilution procedure. In 500 mg/L, the antimicrobial activity was 100%. In addition to these, the biofilm inhibition of NF@FeO(OH) and NC@α-Fe 2 O 3 were investigated against S. aureus and P. aeruginosa and it was found that they showed significant antibiofilm inhibition. It is suggested that additional studies can be continued to be developed and used as an antibacterial according to the results of the nanoparticles after various toxicological test systems.

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“…Unfortunately, there is a dilemma for developing such a bifunctional nanocatalyst (Scheme ). The catalyst for the hydrogenation of nitro compounds requires an electron-rich environment to improve the activity, , while the condensation of amine compounds with β-dicarbonyl compounds often requires a Lewis acid-type catalyst, which has an electron-deficient environment. , Simply mixing the hydrogenation catalyst with Lewis acid will decline the selectivity of nitro hydrogenation inevitably, as the diketones and β-ketoenamines in the cascade reaction mixture are also easily reducible. Therefore, developing a catalyst that can reconcile the contradictory electronic effects for the catalytic hydrogenation of nitro and the in situ condensation with diketones is the key to realizing the cascade synthesis of β-ketoenamines .…”

Section: Introductionmentioning

confidence: 99%

Encapsulating Electron-Rich Pd NPs with Lewis Acidic MOF: Reconciling the Electron-Preference Conflict of the Catalyst for Cascade Condensation via Nitro Reduction

Wang

Tian

et al. 2022

ACS Appl. Mater. Interfaces

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Cascade reactions take advantage of step-saving and facile operation for obtaining chemicals. Herein, catalytic hydrogenation of nitroarene coupled condensation with β-diketone to afford β-ketoenamines is achieved by an integrated nanocatalyst, Pd-e@UiO-66. The catalyst has the structure of an acid-rich metal–organic framework (MOF), UiO-66-encapsulated electron-rich Pd nanoparticles, and it reconciles the electron-effect contradiction of cascade catalytic reactions: catalytic hydrogenation requires an electron-rich catalyst, while condensation requires electron-deficient Lewis acid sites. The catalyst showed good activity, high chemoselectivity, and universal applicability for the synthesis of β-ketoenamines using nitroarenes. More than 30 β-ketoenamines have been successfully prepared with up to 99% yield via the methodology of relay catalysis. The catalyst exhibited excellent stability to maintain its catalytic performance for more than five cycles. Furthermore, we conducted an in-depth exploration of the reaction mechanism with theoretical calculations.

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Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Cited by 20 publications

References 54 publications

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

A comparative study of iron nanoflower and nanocube in terms of antibacterial properties

Encapsulating Electron-Rich Pd NPs with Lewis Acidic MOF: Reconciling the Electron-Preference Conflict of the Catalyst for Cascade Condensation via Nitro Reduction

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