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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 1033 - 1037

DOI: https://doi.org/10.6023/cjoc201909027

Synthesis of 5-Iodomethyl Dihydrofurans via t-Butyl Hydroperoxide-Induced Lodocyclization of Olefinic Dicarbonyl Compounds with I2

  • Quan Jining ,
  • He Xiaoxue ,
  • Yan Xinhuan ,
  • Li Xiaoqing ,
  • Xu Xiangsheng
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  • College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received date: 2019-09-17

  Revised date: 2019-11-23

  Online published: 2020-05-06

Supported by

Project supported by the National Key Research and Development Program of China (No. 2017YFC0210900) and the Innovative Experimental Project of Zhejiang University of Technology (No. SYXM1704).

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Abstract

A new method for the iodocyclization of olefinic dicarbonyl compounds with t-butyl hydroperoxide (TBHP) and I2 was developed. The in situ generated hypoiodous acid and tBuOI were used as active iodine cation reagents. This method allowed the synthesis of polysubstituted 5-iodomethyldihydrofurans under mild reaction conditions with cheap reagents and high atom economy.

Key words： iodocyclization; olefinic dicarbonyl compounds; dihydrofurans; TBHP; I2

Cite this article

Quan Jining , He Xiaoxue , Yan Xinhuan , Li Xiaoqing , Xu Xiangsheng . Synthesis of 5-Iodomethyl Dihydrofurans via t-Butyl Hydroperoxide-Induced Lodocyclization of Olefinic Dicarbonyl Compounds with I2[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 1033 -1037 . DOI: 10.6023/cjoc201909027

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