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

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

研究简报

有机硒催化肟转化为腈或酮

  • 王利敏 ,
  • 李柯 ,
  • 张万轩
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  • 湖北大学有机化工新材料湖北省协同创新中心 有机功能分子合成与应用教育部重点实验室 武汉 430062

收稿日期: 2021-09-22

  修回日期: 2021-12-06

  网络出版日期: 2021-12-31

基金资助

有机功能分子合成与应用教育部重点实验室(KLSAOFM1912)

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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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摘要

1-氟吡啶三氟甲烷磺酸盐(FP-OTf)和二苯基二硒醚在空气中反应生成苯次硒酸和苯亚硒酸, 这种混合物可以催化醛肟和酮肟分别转化腈或酮. 通过改变二苯基二硒醚的用量及其与FP-OTf的物质的量之比, 能够提高以上两类反应的催化效果. 当二苯基二硒醚用量为5 mol%, FP-OTf的用量为4 mol%时, 可以催化醛肟以较高的产率转化为腈(57%~94%), 而在酮肟转化为酮的反应中, 二苯基二硒醚的用量为2.5 mol%, 且与FP-OTf的物质的量之比为1∶1.2时, 产率较高(74%~91%).

关键词： 肟; 腈; 酮; 二苯基二硒醚; 1-氟吡啶三氟甲烷磺酸盐; 催化

本文引用格式

王利敏 , 李柯 , 张万轩 . 有机硒催化肟转化为腈或酮[J]. 有机化学, 2022 , 42(4) : 1235 -1240 . DOI: 10.6023/cjoc202109036

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

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