Cationic Aluminum Complex Catalyzed Synthesis of 2,8-Dioxabicyclo[3.3.1]nonanes

doi:10.6023/cjoc201905009

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3550-3559.DOI: 10.6023/cjoc201905009 Previous Articles Next Articles

阳离子铝化合物催化合成2,8-二氧杂双环[3.3.1]壬烷

杨敏荣, 朱亚楠, 徐凡

苏州大学材料与化学化工学部苏州 215123

收稿日期:2019-05-06 修回日期:2019-07-21 发布日期:2019-08-07
通讯作者: 徐凡 E-mail:xufan@suda.edu.cn
基金资助:
国家自然科学基金（No.21272168）和江苏省高等学校自然科学研究（No.18KJA150007）资助项目.

Cationic Aluminum Complex Catalyzed Synthesis of 2,8-Dioxabicyclo[3.3.1]nonanes

Yang Minrong, Zhu Ya'nan, Xu Fan

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received:2019-05-06 Revised:2019-07-21 Published:2019-08-07
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272168) and the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 18KJA150007).

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Abstract

2,8-Dioxabicyclo[3.3.1]nonane exists in many natural biologically active materials. Cationic aluminum complex[AlCl(CH₃CN)₅]²⁺[(AlCl₄)₂]^2-·CH₃CN can be easily prepared via the reaction of AlCl₃ with CH₃CN at room temperature. It served as efficient catalyst for the tandem Friedel-Crafts alkylation/ketalization reaction of 2-hydroxychalcones with naphthols to produce diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes in moderate to high yields. This method provides a practical process to afford this type of biologically important compounds in good yields using easily available and inexpensive catalyst.

Key words: cationic aluminum complex, Lewis acid, catalysis, 2,8-dioxabicyclo[3.3.1]nonane, synthesis

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Yang Minrong, Zhu Ya'nan, Xu Fan. Cationic Aluminum Complex Catalyzed Synthesis of 2,8-Dioxabicyclo[3.3.1]nonanes[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3550-3559.

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阳离子铝化合物催化合成2,8-二氧杂双环[3.3.1]壬烷

Cationic Aluminum Complex Catalyzed Synthesis of 2,8-Dioxabicyclo[3.3.1]nonanes

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