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

doi:10.6023/cjoc201909027

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 1033-1037.DOI: 10.6023/cjoc201909027 Previous Articles Next Articles

叔丁基过氧化氢和碘介导的烯基化二羰基化合物的碘环化合成5-碘甲基二氢呋喃

全积宁, 何小雪, 严新焕, 李小青, 许响生

浙江工业大学化学工程学院杭州 310014

收稿日期:2019-09-17 修回日期:2019-11-23 发布日期:2020-05-06
通讯作者: 许响生 E-mail:future@zjut.edu.cn
基金资助:
中国国家重点研究发展计划（No.2017YFC0210900）和浙江工业大学创新实验计划（No.SYXM1704）资助项目.

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

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2019-09-17 Revised:2019-11-23 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.

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叔丁基过氧化氢和碘介导的烯基化二羰基化合物的碘环化合成5-碘甲基二氢呋喃

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

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