Nitrobenzene transformations in the carbonylation reaction in the presence of the PdCl2/Fe/I2/Py catalyst system

Skupińska, Jadwiga; Karpińska, Monika

doi:10.1016/j.apcata.2004.02.033

Cited by 20 publications

(10 citation statements)

References 46 publications

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“…2-methylquinoline is probably formed during condensation of aniline with croton aldehyde (Eqs. (5) and (6)) [9,39], in agreement with our previous reports [31,32].…”

Section: Resultssupporting

confidence: 93%

“…In our laboratory was successfully applied the catalytic system PdCl 2 /Fe/I 2 /pyridine for carbonylation of aromatic amines in the presence of nitrobenzene (NB) or molecular oxygen as oxidizing agent to obtain ethyl N-phenylcarbamate (EPC) or N,Ndiphenylurea (DPU) [25,[30][31][32]. No substituent effects (in the aniline ring) on the yield of EPC or DPU in the presence of NB as an oxidizing agent was observed [32].…”

Section: Introductionmentioning

confidence: 92%

“…Mechanism of NB carbonylation proposed by Krogul and Skupinska [19,31,32] includes the formation of aniline (AN) as the first step with the electron transfer from palladium to nitro group of NB as a rate determining step. In general, carbonylation of NB can be considered as a carbonylation of AN with nitrobenzene being an oxidant [19] but mechanism of the carbonylation of AN catalyzed by PdCl 2 (X n Py) 2 complexes in the presence of oxidants other than NB still remains unsolved.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

One pot synthesis of ureas and carbamates via oxidative carbonylation of aniline-type substrates by CO/O2 mixture catalyzed by Pd-complexes

Krogul

Litwinienko

2015

Journal of Molecular Catalysis A: Chemical

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“…2-methylquinoline is probably formed during condensation of aniline with croton aldehyde (Eqs. (5) and (6)) [9,39], in agreement with our previous reports [31,32].…”

Section: Resultssupporting

confidence: 93%

Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

One pot synthesis of ureas and carbamates via oxidative carbonylation of aniline-type substrates by CO/O2 mixture catalyzed by Pd-complexes

Krogul

Litwinienko

2015

Journal of Molecular Catalysis A: Chemical

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“…The addition of 5 mmol of aniline to the PdCl 2 /Fe/I 2 /Py catalytic system resulted in increases in both the reaction rate and carbamate yield [15]. However, when the PdCl 2 /Fe/I 2 /An catalytic system (with pyridine replaced by aniline) was applied, the carbamate yield decreased.…”

Section: The Effect Of Aminementioning

confidence: 94%

“…In two recent papers [15,16] the authors have described the various transformations which have taken place during the carbonylation of nitrobenzene in the presence of the PdCl 2 /Fe/I 2 /Py catalyst system and have proposed intermediate palladium complexes formed in this reaction. Now the authors present preliminary results regarding the role of various catalyst system components.…”

Section: P Hn O 2 + 3co + Etoh → P Hn Hc(o)oetmentioning

confidence: 99%

The effect of the components of the PdCl2/Fe/I2/Py catalytic system on nitrobenzene carbonylation to ethyl N-phenylcarbamate

et al. 2005

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Abstract:The PdCl 2 /Fe/I 2 /Py catalytic system (Py -pyridine), reported to be highly active in the reaction of nitrobenzene carbonylation to ethyl phenylcarbamate was studied. The present paper describes the role of catalyst components and its effect on the activity and selectivity of the catalyst. The increase in the amount of PdCl 2 in the system while retaining a constant level of the other catalyst components, results in the increase of both carbamate and aniline yields. The increase in the amount of iron while retaining the other components constant, initially causes an increase in the carbamate yield; however, at Fe : Pd ratios higher than 36, the carbamate yield remains constant. The change in the amount of iron has no effect on the amount of aniline formed in the system. An increase in the amount of iodine in the system while retaining the other components constant, results in a decrease in carbamate yield and a considerable increase in the aniline yield of the reaction products.

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Synthesis of Carbamates from Alkyl Bromides and Secondary Amines Using Silver Carbonate

Acharya

Mal²,

Kilaru³

et al. 2020

Eur J Org Chem

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show abstract

Nitrobenzene transformations in the carbonylation reaction in the presence of the PdCl2/Fe/I2/Py catalyst system

Cited by 20 publications

References 46 publications

One pot synthesis of ureas and carbamates via oxidative carbonylation of aniline-type substrates by CO/O2 mixture catalyzed by Pd-complexes

One pot synthesis of ureas and carbamates via oxidative carbonylation of aniline-type substrates by CO/O2 mixture catalyzed by Pd-complexes

The effect of the components of the PdCl2/Fe/I2/Py catalytic system on nitrobenzene carbonylation to ethyl N-phenylcarbamate

Synthesis of Carbamates from Alkyl Bromides and Secondary Amines Using Silver Carbonate

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