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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 9: 2814 - 2822

DOI: https://doi.org/10.6023/cjoc202204057

ARTICLES

A Solvent-Regulated Dediazotized Oxygenation of α-Aryl α-Diazoesters and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

  • Runhong Jia ,
  • Shuai Liu ,
  • Shichao Wang ,
  • Wenjuan Hao ,
  • Bo Jiang
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  • a Elementary Education College, Lianyungang Normal College, Lianyungang, Jiangsu 222006
    b School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
* Corresponding authors. E-mail: ;

Received date: 2022-04-24

  Revised date: 2022-06-16

  Online published: 2022-06-29

Supported by

National Natural Science Foundation of China(21971090)

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Abstract

A new metal-free, solvent-regulated dediazotized oxygenation of α-aryl α-diazo esters and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is reported. The reaction of α-aryl α-diazo esters and DDQ in 2∶1 molar ratio in dichloromethane (DCM) underwent double dediazotized O—H bond insertion reactions to access α,α'-(1,4- phenyldioxy)diesters as major products, whereas a series of structurally complex α,α-diaryloxy esters were provided with moderate to good yields when the reaction of these substrates in 3∶2 molar ratio in dichloroethane (DCE) proceeded through a double dediazotized O—H bond insertion and dediazotized deoxygenation cascade. The controlled experiments confirmed that the hydrogen atom is from water during O—H bond insertion process. In addition, the reaction featured mild conditions, simple operation and controllable chemoselectivity without any catalyst.

Key words： oxygenation; dediazotization; chemoselectivity; divergent synthesis

Cite this article

Runhong Jia , Shuai Liu , Shichao Wang , Wenjuan Hao , Bo Jiang . A Solvent-Regulated Dediazotized Oxygenation of α-Aryl α-Diazoesters and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)[J]. Chinese Journal of Organic Chemistry, 2022 , 42(9) : 2814 -2822 . DOI: 10.6023/cjoc202204057

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