Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp3)—H Activation of Cyclic Ethers

doi:10.6023/cjoc202312021

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1978-1986.DOI: 10.6023/cjoc202312021 Previous Articles Next Articles

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多相铁催化环状醚C(sp³)—H键活化的芳基烯烃氧烷基化

于蕾^a, 盛康^b, 李亭^a^,^*(), 唐从辉^b^,^*()

a 南阳师范学院化学与制药工程学院河南南阳 473061
b 华中科技大学化学与化工学院能量转换与存储材料化学教育部重点实验室材料化学与服役失效湖北省重点实验室武汉 430074

收稿日期:2023-12-22 修回日期:2024-02-01 发布日期:2024-02-27
基金资助:
国家自然科学基金(22371083); 国家自然科学基金(22001086)

Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp³)—H Activation of Cyclic Ethers

Lei Yu^a, Kang Sheng^b, Ting Li^a,*(), Conghui Tang^b,*()

a College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473061
b Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074

Received:2023-12-22 Revised:2024-02-01 Published:2024-02-27
Contact: * E-mail: chemlt2015@nynu.edu.cn; ctang@hust.edu.cn
Supported by:
National Natural Science Foundation of China(22371083); National Natural Science Foundation of China(22001086)

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Abstract

Alkene difunctionalization is an important route to construct new chemical bonds over the olefin double bond, oxyalkylation reaction of olefins will provide C—C bond and C—O bond forming products. The current oxyalkylation methods rely in employing tert-butyl hydroperoxide as the oxidant. Therefore, developing an aerobic oxidation system for this transformation is highly desired. Herein, an unprecedented heterogeneous iron catalyzed oxyalkylation of styrene derivatives under mild conditions was reported, using air as oxidant and oxygen source. Detailed catalyst characterization, substrate scope and mechanistic studies were carried out and a proposed mechanism was given.

Key words: alkene, difunctionalization, C(sp³)—H activation, heterogeneous iron catalysis

Cite this article

Lei Yu, Kang Sheng, Ting Li, Conghui Tang. Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp³)—H Activation of Cyclic Ethers[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1978-1986.

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Fig. & Tab. 7

Scheme 1. Transition metal-catalyzed alkene oxyalkylation reactions

Figure 1. Characterizations of Fe@Fe3O4-N/C

Table 1. Reaction conditions optimizationa

Table 2. Substrate scope of vinylarenesa

Table 3. Substrate scope of cyclic ethersa

Scheme 2. Mechanistic studies and control experiments

Scheme 3. Proposed mechanism of oxyalkylation reaction of vinylarenes

References 17

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多相铁催化环状醚C(sp³)—H键活化的芳基烯烃氧烷基化

Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp³)—H Activation of Cyclic Ethers

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Fig. & Tab. 7

References 17

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多相铁催化环状醚C(sp3)—H键活化的芳基烯烃氧烷基化