Advances on the Synthesis of Aryl Ethers via Dehydrogenative Coupling

doi:10.6023/cjoc201904011

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2735-2743.DOI: 10.6023/cjoc201904011 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019

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脱氢偶联制备芳基醚方法的研究进展

唐灏^a, 骆钧飞^a^*(), 解攀^b^*()

^a 宁波大学材料科学与化学工程学院宁波 315211
^b 陕西科技大学化学与化工学院陕西省轻化工助剂重点实验室西安 710021

收稿日期:2019-04-04 修回日期:2019-05-09 发布日期:2019-06-06
通讯作者: 骆钧飞,解攀 E-mail:luojunfei@nbu.edu.cn;pan.xie@sust.edu.cn
基金资助:
浙江省自然科学基金(LQ19B020002);宁波市自然科学基金(2018A610241);浙江省教育厅(Y201839228);宁波大学王宽诚幸福基金资助项

Advances on the Synthesis of Aryl Ethers via Dehydrogenative Coupling

Tang Hao^a, Luo Junfei^a^*(), Xie Pan^b^*()

^a School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211
^b Shaanxi Key Laboratory of Chemistry Additives for Industry, College of Chemistry and Chemistry Engineering, Shaanxi University of Science & Technology, Xi?an 710021

Received:2019-04-04 Revised:2019-05-09 Published:2019-06-06
Contact: Luo Junfei,Xie Pan E-mail:luojunfei@nbu.edu.cn;pan.xie@sust.edu.cn
Supported by:
Project supported by the Natural Science Foundation of Zhejiang Province(LQ19B020002);The Municipal Natural Science Foundation of Ningbo City(2018A610241);The Education Foundation of Zhejiang Province(Y201839228);The K. C. Wong Magna Fund in Ningbo University

Aryl ethers are important central motifs that are abundant in many natural products and drug molecules, as well as versatile building blocks for organic synthesis. Aryl ethers were usually synthesized through the coupling reactions between leaving group substituted arenes and alcohols. However, the introduction of leaving group requires extra synthetic operation and produces lots of wastes. Over the past decade, the method for the synthesis of aryl ethers via C—H alkoxylation or aryloxylation has received much attention due to its potential as an atom and step efficient methodology. Herein, the research advances on the synthesis of aryl ethers through dehydrogenative coupling are reviewed. The detailed substrate scopes and reaction mechanisms, as well as the limitations of current procedures and the prospects for the future, are discussed.

Key words: aryl ether, dehydrogenative coupling, C—H activation, phenol, alcohol

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Tang Hao, Luo Junfei, Xie Pan. Advances on the Synthesis of Aryl Ethers via Dehydrogenative Coupling[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2735-2743.

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Fig. & Tab. 12

Figure 1. Important molecules containing aryl ethers

Scheme 1. Methods for the preparation of aryl ethers

Scheme 2. Mechanism for the synthesis of aryl ethers via Pd- catalyzed C—H activation

Scheme 3. Pd-catalyzed C—O cyclization

Scheme 4. C—H functionalization for the synthesis of dihdro- benzofuran derivatives

Scheme 5. Mechanism for Cu-mediated C—H alkoxylation

Scheme 6. Catalytic cycle for Cu-catalyzed C—H alkoxylation

Scheme 7. Mechanism for Cu(I)-catalyzed C—H methoxylation.

Scheme 8. Catalytic cycle for Co-catalyzed C—H alkoxylation

Scheme 9. Mechanism for Cu-catalyzed intramolecular aryloxylation.

Scheme 10. Synthesis for the benzodiazepine derivative

Scheme 11. Ammonium tetrabutyl iodide catalyst dehydrogenative aryl intramolecular mechanism

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脱氢偶联制备芳基醚方法的研究进展

Advances on the Synthesis of Aryl Ethers via Dehydrogenative Coupling

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