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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 4: 1235 - 1240

DOI: https://doi.org/10.6023/cjoc202109036

NOTES

Organoselenium-Catalyzed Conversion of Oximes to Nitriles or Ketones

  • Liming Wang ,
  • Ke Li ,
  • Wanxuan Zhang
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  • Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei Collaborative Innovation Center for Advanced Organic Chemical Material, Hubei University, Wuhan 430062
* E-mail:

Received date: 2021-09-22

  Revised date: 2021-12-06

  Online published: 2021-12-31

Supported by

Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education(KLSAOFM1912)

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Abstract

Phenylselenenic acid and phenylseleninic acid were formed in situ in the reaction of diphenyl diselenide with 1-fluoropyridine trifluoromethane sulfonate (FP-OTf) in air. This mixture can catalyze the conversion of aldoxime to nitrile or ketoxime to ketone, respectively. The catalytic effect on those two kinds of reactions can be improved by changing the amount of diphenyl diselenide and the ratio of diphenyl diselenide to FP-OTf. Nitriles were obtained from the open-air reaction of aldoxime catalyzed by the mixture of diphenyl diselenide (5 mol%) and FP-OTf (4 mol%) with the yields of 57%~94%. In the conversion of ketoximes to ketones, higher yields of ketones (74%~91%) were obtaied when the ratio of diphenyl diselenide to FP-OTf was 1∶1.2 and the dosage of diphenyl diselenide was 2.5 mol%.

Key words： oxime; nitrile; ketone; diphenyl diselenide; 1-fluoropyridine trifluoromethane sulfonate; catalysis

Cite this article

Liming Wang , Ke Li , Wanxuan Zhang . Organoselenium-Catalyzed Conversion of Oximes to Nitriles or Ketones[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1235 -1240 . DOI: 10.6023/cjoc202109036

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