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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 12: 4332 - 4339

DOI: https://doi.org/10.6023/cjoc202207044

ARTICLES

Intermolecular Acylation with Acylphosphonates as Alkyl Radical Receptor under Metal-Free Conditions

  • Jing Fang ,
  • Qingqiang Min ,
  • Haitao Qin ,
  • Feng Liu
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  • a Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, Suzhou 215123
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
*E-mail: ;

Received date: 2022-07-30

  Revised date: 2022-08-26

  Online published: 2022-09-09

Supported by

National Natural Science Foundation of China(22171200)

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Abstract

As one of the central functional groups in organic chemistry, carbonyl skeleton can be achieved by many ways, but the intermolecular radical reaction using acyl phosphonate as acyl donor is rarely reported. The acylation reaction between acyl phosphonate as a free radical acceptor and three free radical donors, alkyl aldehyde, Hans ester and alkane, was studied under thermochemical and photochemical conditions, respectively. When alkyl aldehydes and alkanes were used as radical precursors, the intermolecular acylation reaction could proceed smoothly under the conditions of microwave heating and the presence of oxidants. When Hantzsch esters were used as the radical precursors, the intermolecular acylation reaction could take place smoothly under UV irradiation at room temperature.

Key words： acylphosphonate; radical acceptor; intermolecular acylation reaction

Cite this article

Jing Fang , Qingqiang Min , Haitao Qin , Feng Liu . Intermolecular Acylation with Acylphosphonates as Alkyl Radical Receptor under Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4332 -4339 . DOI: 10.6023/cjoc202207044

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