Bis(NHC)-Pd(II) and Pd(0) complexes supported on magnetic SBA-15 for the selective aerobic oxidation of benzyl alcohols to benzaldehydes and reduction of nitroarenes

Fekri, Somayeh; Mansoori, Yagoub; Bezaatpour, Abolfazl

doi:10.1016/j.jorganchem.2023.122724

Cited by 6 publications

(1 citation statement)

References 85 publications

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.87−7.68 (m, 1H), 7.68−7.53 (m, 1H), 7.47 (ddd, J = 7.8, 1.9, 0.9 Hz, 1H), 7.40−7.28 (m, 1H), 3.26−3.02 (m, 2H), 2.77−2.58 (m, 2H); (2E)-3-Phenylprop-2-enal (4r). 27 The crude mixture was purified by column chromatography on a silica gel (hexane/EtOAc as an eluent), and product 4r (16.4 mg, 62% yield) was obtained as a colorless liquid. 1 H NMR (500 MHz, CDCl 3 ) δ 9.71 (d, J = 7.6 Hz, 1H), 7.56 (s, 2H), 7.51−7.40 (m, 4H), 6.73 (dd, J = 15.9, 7.6 Hz, 1H); 13 C{ 1 H} NMR (126 MHz, CDCl 3 ) δ 193.9, 152.9, 134.2, 131.4, 129.2, 128.7, 128.6.…”

Section: -Bromobenzaldehyde (4g) 5cmentioning

confidence: 99%

Phenalenyl-Based Photocatalyst for Bioinspired Oxidative Dehydrogenation of N-Heterocycles and Benzyl Alcohols

Pathania,

Roy

2024

J. Org. Chem.

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The environmental benefits of molecular oxygen as the oxidizing agent in oxidation reactions that synthesize fine chemicals cannot be overstated. Increased interest in developing robust photocatalysts is stimulated by the fact that the current photocatalytic transformation boom has made previously inaccessible synthetic approaches possible. Motivated by enzymatic catalysis, employing a reusable phenalenyl-based photocatalyst, we have successfully developed oxidative dehydrogenation utilizing molecular oxygen as a greener oxidant. Under photoinduced oxidative dehydrogenation conditions, different types of saturated Nheterocycles and alcohols were successfully dehydrogenated. The versatility of this bioinspired protocol is demonstrated by the fact that a wide variety of N-heteroaromatics, such as quinoline, carbazole, quinoxaline, acridine, and indole derivatives, as well as aldehydes and ketones, were successfully synthesized. Detailed mechanistic studies validate the proposed mechanism. Fluorescence lifetime and CV experiments revealed the crucial role of water on the efficiency of the reaction. The present protocol also provides chemoselectivity and scalability, leading to superior results and allowing for the functionalization of bioactive molecules at a late stage in a sustainable manner.

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Section: -Bromobenzaldehyde (4g) 5cmentioning

confidence: 99%

Phenalenyl-Based Photocatalyst for Bioinspired Oxidative Dehydrogenation of N-Heterocycles and Benzyl Alcohols

Pathania,

Roy

2024

J. Org. Chem.

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Oxime Palladacycle Supported on Magnetic Meoporous Silica: An Efficient Catalyst for Copper‐Free Acyl Sonogashira Reaction

Ghahramani,

Mansoori,

John

2024

ChemNanoMat

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The catalytic activity of the supported bis(oxime palladacycle) catalyst was evaluated in the acyl Sonogashira reaction. The reaction conditions, such as solvent, base, and palladium content, were screened to achieve the best catalytic performance. Tetrahydrofuran (THF) solvent, triethylamine (Et3N) base, and the reaction temperature of 110°C were found to be ideal for achieving high yields of the desired products. Furthermore, a catalyst loading of only 0.22 mol% palladium was sufficient to achieve good conversion. Broad ranges of aryl acetylenes and benzoyl chlorides were successfully coupled to give the desired acetylenic ketones. The reaction appeared to proceed efficiently using a small amount of catalyst. The magnetic property of the catalyst allowed for easy separation using an external magnet. The catalyst was stable and reused for multiple reaction runs without a significant deactivation. After seven cycles, the catalyst maintained over 90% of its initial catalytic activity.

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Pd(II)‐Catalyzed Aerobic Alcohol Oxidation for Multicomponent Synthesis of 2,3‐Dihydroquinazolin‐4(1H)‐ones in Water

Kobayashi,

Kataoka,

Nakayama

et al. 2024

ChemistrySelect

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We describe a multicomponent reaction between isatoic anhydrides, alkylamines and benzylic alcohols using Pd(II)/TPPMS catalyst with cocatalytic Cu(II) salt in water. This cascade reaction involves the catalytic dehydrogenation of benzyl alcohol to benzaldehyde under aerobic conditions, followed by cyclocondensation with in situ generated 2‐aminobenzamides, allowing rapid access to 2,3‐dihydroquinazolin‐4(1H)‐ones (DHQs). This practical method enables direct access to a series of DHQs without strong bases and hazardous oxidants. Mechanistic studies reveal that the multicomponent reaction is first order with respect to the concentrations of benzyl alcohol and catalysts, and proceeds independently of the concentration of the 2‐aminobenzamide intermediate.

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Bis(NHC)-Pd(II) and Pd(0) complexes supported on magnetic SBA-15 for the selective aerobic oxidation of benzyl alcohols to benzaldehydes and reduction of nitroarenes

Cited by 6 publications

References 85 publications

Phenalenyl-Based Photocatalyst for Bioinspired Oxidative Dehydrogenation of N-Heterocycles and Benzyl Alcohols

Phenalenyl-Based Photocatalyst for Bioinspired Oxidative Dehydrogenation of N-Heterocycles and Benzyl Alcohols

Oxime Palladacycle Supported on Magnetic Meoporous Silica: An Efficient Catalyst for Copper‐Free Acyl Sonogashira Reaction

Pd(II)‐Catalyzed Aerobic Alcohol Oxidation for Multicomponent Synthesis of 2,3‐Dihydroquinazolin‐4(1H)‐ones in Water

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