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CC BY-NC-ND 4.0 · SynOpen 2022; 06(03): 158-163
DOI: 10.1055/a-1843-6641
paper

The Synthesis of 5-Hydroxybenzofurans via Tandem In Situ Oxidative Coupling and Cyclization

Zhongren Lin‡
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, Shanghai 200237, P. R. of China
,
Lingfeng Tong‡
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, Shanghai 200237, P. R. of China
,
Hong Qiu
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, Shanghai 200237, P. R. of China
,
Zheyao Li
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, Shanghai 200237, P. R. of China
,
Lunhua Shen
c   Mianyang Vendinor Pharmaceutical Co., Ltd, Mianyang 621010, P. R. of China
,
Niangen Chen∗
b   School of Pharmacy, Hainan Medical University, Haikou 571199, P. R. of China
,
Xinhong Yu  ∗
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, Shanghai 200237, P. R. of China
› Author AffiliationsWe gratefully acknowledge financial support from the National Natural Science Foundation of China (20972051 and 21476078, X.-H.Y.) and the Science and Technology Commission of Shanghai Municipality (No. 12431900902, X.-H. Y.).
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Abstract

A series of 5-hydroxybenzofurans have been prepared by PIDA-mediated oxidation and coupling cyclization of β-dicarbonyl compounds and hydroquinones. The reaction functionalizes C(sp2)–H of hydroquinones directly with yields of target molecules up to 96%.

Key words

5-hydroxybenzofurans - oxidation - dearomatization - aromatic C(sp2)–H functionalization - one-pot reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1843-6641.
  • Supporting Information


Publication History

Received: 28 February 2022

Accepted after revision: 27 April 2022

Accepted Manuscript online:
04 May 2022

Article published online:
19 July 2022

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