Recyclable polymerized Lewis acid poly-BPh(C6F5)2 catalyzed selective N-formylation and N-methylation of amines with carbon dioxide and phenylsilanes

Zhai, Gaowen; Liu, Qiang; Ji, Jialan; Wu, Youting; Geng, Jiao; Hu, Xingbang

doi:10.1016/j.jcou.2022.102052

Cited by 9 publications

(7 citation statements)

References 97 publications

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“…A large number of heterogeneous catalytic routes have been developed for N -formylation transformations in which various formylating agents were explored such as CO 2 , − HCOOH, − HCHO, etc. However, several bottlenecks still need to be addressed in this field: (1) discovery of new formylating agents.…”

Section: Resultsmentioning

confidence: 99%

“…In addition to the formic acid, CO 2 is the most frequently employed formylating reagent in heterogeneous catalytic systems. It should be noted that excess PhSiH 3 ,,, or high-pressure H 2 , in documented literature is necessary as a hydrogen source, which may cause high cost and increase the potential danger of the practice. (2) Exploration of stable and readily available heterogeneous catalysts.…”

Section: Resultsmentioning

confidence: 99%

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Donor–Acceptor-Conjugated Porous Polymer for Photopromoted N–H Formylation of Secondary Amines: Efficient In Situ N-Heterocyclic Carbene Catalysis in Radical Manner

Bai,

Zheng,

et al. 2024

ACS Catal.

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The photogenerated reactive oxygen species (ROSs) in N-heterocyclic carbene (NHC)-based heterogeneous photocatalysis hold promise for addressing the challenge of fostering Breslow-derived radicals. In this study, two conjugated porous polymers (CPPs), namely, Im-PCPP-1 and Im-PCPP-2, decorated with donor−acceptor-type porphyrin and imidazole/ imidazolium moieties, are synthesized via Suzuki−Miyaura coupling reaction. Importantly, the ionization of the imidazole monomer effectively tunes the push−pull effect of D−A building blocks and the band structure of Im-PCPPs. On this basis, Im-PCPP-2 with ionized imidazolium exhibits good catalytic activity toward oxidative N-formylation of diverse secondary amines through the cooperation of photoredox and in situ NHC catalysis in a radical manner, where acetaldehyde serves as the carbon source of formylation. Experimental and calculation results suggest that photogenerated multiple ROS play crucial roles: hydroxide OH − as in situ base to generate NHC; hydroxyl radical • OH as hydrogen atom transfer abstractors to produce aza-Breslow-derived radicals and as radical partners for cross-coupling; singlet oxygen 1 O 2 as oxidant to convert aza-Breslow-derived radical into cyclic peroxide. It is noteworthy that the photochemical process has achieved efficient conversion of acetaldehyde and its derivatives to high-value-added N-formamides.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Donor–Acceptor-Conjugated Porous Polymer for Photopromoted N–H Formylation of Secondary Amines: Efficient In Situ N-Heterocyclic Carbene Catalysis in Radical Manner

Bai,

Zheng,

et al. 2024

ACS Catal.

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“…For the past decade, various Lewis acid catalysts have been developed for the reductive carbon dioxide fixation to formamides. − ,− For example, homogeneous catalysts bearing Zn, Cu, and Fe have been reported with TONs of 30–198 and TOFs of 1–33 h –1 for the reductive carbon dioxide fixation with N -methyl- N -phenylamine to N -methyl- N -phenylformamide at temperatures of 25–60 °C (refer to Table S2 for recent homogeneous catalytic systems). − …”

Section: Resultsmentioning

confidence: 99%

“…Recently, the reductive carbon dioxide fixation to formamides has attracted significant attention from scientists due to its mild reaction conditions. − The reaction of carbon dioxide with amines in the presence of silanes can induce the formation of formamides. Efficient Lewis acid catalysts enable this conversion to take place even at room temperature. − …”

Section: Introductionmentioning

confidence: 99%

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Kim,

Jang,

et al. 2024

ACS Appl. Nano Mater.

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This work suggests an engineering methodology for catalytic 2D materials to achieve more efficient catalytic systems. Zinc gallate (ZnG), a Lewis acidic material with a thin 2D morphology, can easily form aggregates through layer–layer packing. Inner parts of ZnG aggregates would have difficulty in interacting with substrates. By coating hollow microporous organic polymer (H-MOP) supports with ZnG, the catalytic performance of ZnG can be enhanced due to facilitated contact of substrates with Zn species in shells. H-MOP@ZnG-2 with an optimal ZnG coating showed a much enhanced catalytic performance for the reductive carbon dioxide fixation with amines to formamides compared with ZnG. Various amines can be utilized in the reductive carbon dioxide fixation to formamides. In addition, H-MOP@ZnG-2 showed recyclability, maintaining its catalytic performance for five successive reactions.

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“…In this study, a new type of non-ionic hydrophilic polypeptide called poly (n-methylated glycine) ( 18 , 19 ) or Polysarcosine (PSar) was used in the delivery of chemotherapeutic drugs by polymeric nanoparticles; which is the best alternative to corona-forming polymer, poly (ethylene glycol) (PEG) ( 20 ). Apart from PSar, the Poly D, L-lactic-co-glycolic acid (PLGA) ( 21 ) was also used; due to its excellent biodegradability and biocompatibility properties it is an excellent choice for drug delivery.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the therapeutic potential of cabozantinib-loaded poly D,L-lactic-co-glycolic acid and polysarcosine nanoparticles in inducing apoptosis and cytotoxicity in human HepG2 hepatocellular carcinoma cell lines and in vivo anti-tumor activity in SCID female mice

Bhattacharya

Parihar²,

Prajapati³

2023

Front. Oncol.

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IntroductionThe study aimed to develop a nano-based drug delivery system for the treatment of hepatocellular carcinoma (HCC), a type of liver cancer that accounts for 90% of all liver malignancies. The study focused on the use of cabozantinib (CNB), a potent multikinase inhibitor that targets the VEGF receptor 2, as the chemotherapeutic drug. We developed CNB-loaded nanoparticles made from Poly D, L-lactic-co-glycolic acid, and Polysarcosine (CNB-PLGA-PSar-NPs) for use in human HepG2 cell lines.MethodsBy O/W solvent evaporation method, the polymeric nanoparticles were prepared. The various techniques, such as photon correlation spectroscopy, scanning electron microscopy, and transmission electron microscopy were used, to determine the formulation's particle size, zeta potential, and morphology. SYBR Green/ROX qPCR Master Mix and RT-PCR equipment used to measure liver cancer cell line and tissue mRNA expression and MTT assay to test HepG2 cell cytotoxicity. Cell cycle arrest analysis, annexin V assay, and ZE5 Cell Analyzer apoptosis assay were also performed.ResultsThe results of the study showed that the particle diameters were 192.0 ± 3.67 nm with 0.128 PDI and -24.18 ± 3.34 mV zeta potential. The antiproliferative and proapoptotic effects of CNB-PLGA-PSar-NPs were evaluated using MTT and flow cytometry (FCM). The IC50 value of CNB-PLGA-PSar-NPs was 45.67 µg/mL, 34.73 µg/mL, and 21.56 µg/mL for 24, 48, and 72 h, respectively. The study also found that 11.20% and 36.77% of CNB-PLGA-PSar-NPs-treated cells were apoptotic at 60 µg/mL and 80 µg/mL, respectively, suggesting that the nanoparticles were effective in inducing apoptosis in the cancer cells. It can also conclude that, CNB-PLGA-PSar-NPs inhibit human HepG2 hepatocellular carcinoma cells and kill them by upregulating the tumour suppressor genes MT1F, MT1X, and downregulating MTTP, APOA4. Further in vivo antitumor activity was well reported in SCID female mice.DiscussionOverall, this study suggests that the CNB-PLGA-PSar-NPs are a promising drug delivery system for the treatment of HCC, and further research is needed to investigate their potential in clinical treatment.

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Recyclable polymerized Lewis acid poly-BPh(C6F5)2 catalyzed selective N-formylation and N-methylation of amines with carbon dioxide and phenylsilanes

Cited by 9 publications

References 97 publications

Donor–Acceptor-Conjugated Porous Polymer for Photopromoted N–H Formylation of Secondary Amines: Efficient In Situ N-Heterocyclic Carbene Catalysis in Radical Manner

Donor–Acceptor-Conjugated Porous Polymer for Photopromoted N–H Formylation of Secondary Amines: Efficient In Situ N-Heterocyclic Carbene Catalysis in Radical Manner

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Unveiling the therapeutic potential of cabozantinib-loaded poly D,L-lactic-co-glycolic acid and polysarcosine nanoparticles in inducing apoptosis and cytotoxicity in human HepG2 hepatocellular carcinoma cell lines and in vivo anti-tumor activity in SCID female mice

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Recyclable polymerized Lewis acid poly-BPh(C6F5)2 catalyzed selective N-formylation and N-methylation of amines with carbon dioxide and phenylsilanes

Cited by 9 publications

References 97 publications

Donor–Acceptor-Conjugated Porous Polymer for Photopromoted N–H Formylation of Secondary Amines: Efficient In Situ N-Heterocyclic Carbene Catalysis in Radical Manner

Donor–Acceptor-Conjugated Porous Polymer for Photopromoted N–H Formylation of Secondary Amines: Efficient In Situ N-Heterocyclic Carbene Catalysis in Radical Manner

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO2 Fixation to Formamides

Unveiling the therapeutic potential of cabozantinib-loaded poly D,L-lactic-co-glycolic acid and polysarcosine nanoparticles in inducing apoptosis and cytotoxicity in human HepG2 hepatocellular carcinoma cell lines and in vivo anti-tumor activity in SCID female mice

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Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides