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Lah, Myoung Soo
Nanoporous Materials Lab
Research Interests
  • Metal-Organic Frameworks (MOFs)

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Imidazolium and phosphonium alkylselenites for the catalytic oxidative carbonylation of amines: Mechanistic studies

Cited 28 times inthomson ciCited 31 times inthomson ci
Title
Imidazolium and phosphonium alkylselenites for the catalytic oxidative carbonylation of amines: Mechanistic studies
Author
Kim, HSKim, YJBae, JYKim, SJLah, Myoung SooChin, CS
Keywords
TEMPERATURE IONIC LIQUIDS; CARBAMATE ESTERS; CARBON-MONOXIDE; N,N'-DIPHENYLUREA SYNTHESIS; AROMATIC-AMINES; ANILINE; PALLADIUM; SYSTEM; CO; HYDROFORMYLATION
Issue Date
200306
Publisher
AMER CHEMICAL SOC
Citation
ORGANOMETALLICS, v.22, no.12, pp.2498 - 2504
Abstract
The reactions of KSeO2(OCH3) (1) in methanol with [Rmim]Cl (Rmim = 1-alkyl-3-methylimidazolium) at room temperature give imidazolium-based ionic liquids containing methylselenite anion, [Rmim] [SeO2(OCH3)] (2a, R = n-C4H9; 3a, R = C2H5; 4a, R = CH3) respectively. Similarly, phosphonium methylselenites, [R4P][SeO2(OCH3)] (6a, R = n-butyl; 7a, R = ethyl) were prepared by reacting 1 with tetraalkylphosphonium bromides. The methoxy groups in imidazolium and phosphonium methylselenites were easily replaced by other alkoxy groups upon interaction with various alcohols. [1,3-dimethylimidazolium] [SeO2-(OCH3)] (4a) is slowly transformed into [1,3-dimethylimidazolium](2)[Se2O5] (5a) in the absence of methanol. An X-ray study reveals that 5a is a dimeric selenium complex consisting of two 1,3-dimethylimidazolium cations and Se2O52- anion. All the ionic liquid compounds containing methylselenite anion show surprisingly high activity for the oxidative carbonylation of aniline, even at temperatures as low as 40 degreesC, to give diphenylurea in high yield. The effects of molar ratio of aniline to catalyst, temperature, and solvent have been investigated. The plausible mechanism for the carbonylation reaction of aniline based on the H-1 and C-13 NMR studies using 3a is presented.
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DOI
http://dx.doi.org/10.1021/om030005f
ISSN
0276-7333
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