Transition Metal Catalyzed Carbonylation of Nitrobenzene for the Synthesis of N,N'-diphenylurea

균일계 전이금속 촉매를 이용한 니트로벤젠의 카르보닐화 반응 연구: N,N'-디페닐우레아 합성

  • Received : 1999.09.04
  • Accepted : 1999.10.21
  • Published : 1999.11.10

Abstract

An investigation was made of the effect of various transition metal catalysts, ligands, and a promoter on the synthesis of N,N'-diphenylurea(DPU) from nitrobenzene, aniline, and carbon monoxide. Homogeneous Pd and Ni catalysts were found to be highly efficient, giving almost quantitative isolated DPU yields at 100% nitrobenzene conversion. Bidentate ligand, 1,3-bis(diphenylphosphino)proane(dppp) showed much improved activity and significantly different reactivity relative to the usual monodentate $PPh_3$ ligand in the presence of Ni and Pd catalysts. These results were inferred to the effect of the cis coordination of bidentate dppp ligand on the metal. The use of a promoter $Et_4NCl$ was indispensable in the case of $PPh_3$, yet inhibited the reaction if used with dppp. It was possible to reuse the Pd-dppp catalyst system, although the catalytic activity was reduced slowly.

Keywords

carbonylation;N,N'-diphenylurea;nitrobenzene;aniline

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Acknowledgement

Supported by : 한국학술진흥재단