Polystyrene‐Supported Palladium (Pd@PS)‐Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2‐Aryl Quinazolinones

Ram, S. Raja; Shaifali, -; Chauhan, Arvind Singh; Sheetal, .; Sharma, Ajay; Das, Pralay

doi:10.1002/chem.201902776

Cited by 29 publications

(8 citation statements)

References 50 publications

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“…In 2019, Das and colleagues in order to develop a convenient and efficient method for the synthesis of quinazolinone (Scheme 15). [38] In this reaction, to replace oxalic acid with N ‐formylsaccharin as CO source only gave the desired quinazolinone ( 34 ) in 17 % yield.…”

Section: Carbonylation Productsmentioning

confidence: 97%

N‐Formylsaccharin as a CO Source: Applications and Recent Developments

et al. 2021

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This review describes the research progress of the N‐formylsaccharin as a newly efficient and environmentally friendly carbon monoxide (CO) surrogate in the carbonylation reactions including the synthesis of aldehydes, esters, ketones, acyl fluorides or other reactions. Besides, its advantages in term of inexpensive, ease of handling and stable on storage significantly enhance practicality of the approach in laboratory scale.

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Section: Carbonylation Productsmentioning

confidence: 97%

N‐Formylsaccharin as a CO Source: Applications and Recent Developments

et al. 2021

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“…Further, polystyrene supported palladium nanoparticles (Pd@PS) catalyst was applied by our group for the synthesis of quinanozolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source (Scheme 56). [80] We have applied economic, bench stable and solid oxalic acid as ex situ CO source using DLV (Double Layer Vial) system for carbonylation reaction to avoid the formation of side products. Additionally, simple catalyst preparation, catalyst recovery up to 5 cycles, wide substrate scope in good to excellent yields of products are the added advantages of the protocols (26 examples, 55-91 % yields).…”

Section: Quinazolinones Synthesismentioning

confidence: 99%

Supported Palladium Catalyzed Carbonylative Coupling Reactions using Carbon Monoxide as C1 Source

Shaifali

Sheetal

Das

2021

The Chemical Record

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The carbonylative reactions of aryl halides, boronic acids, amines, activated alkene and alkynes under CO and supported palladium catalyzed conditions are very popular reactions for the synthesis of bioactive molecules, pharmaceuticals, polymers, peptides, intermediates and fine chemicals synthesis. Due to cost effectiveness and easy handling of recyclable supported palladium catalyst, it became more popular among researchers either working in academic institute or industry. In recent years, irrespective of poisoning effect of CO with palladium as major limitation, several advancements have been done through surface selection, designing and condition improvement to achieve high yield in the area of carbonylative coupling reactions. We hope this review will be helpful as a ready reference of last 20 years in the field of CO insertion reactions using diverse range of supported palladium catalysts under carbon monoxide or its sources as C1 source.

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“…289～ 291 ℃ (Lit. [18] 275 ～ 277 ℃ ); 1 H NMR (400 MHz, DMSO-d 6 ) δ: 12.71 (s, 1H), 8.32 (d,J＝8.4 Hz,2H),8.18 (d,J＝8.0 Hz,1H),8.11 (d,J＝8.4 Hz,2H),7.87 (d,J＝ 7.6 Hz,1H),7.78 (d,J＝8.0 Hz, 1H), 7.56 (t, J＝7.6 Hz, 1H), 3.91 (s, 3H); 13 C NMR (101 MHz, DMSO-d 6 ) δ: 166. 2,162.8,152.0,149.0,135.1,132.2,129.7,128.7,128.0,127.5,126.4,121.6,phenyl)-4(3H)-quinazolinone (2i): 45.1 mg (78% yield).…”

Section: General Informationmentioning

confidence: 99%