Recent Advances in the Synthesis of Dibenzothiophenes

doi:10.6023/cjoc202006032

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 94-104.DOI: 10.6023/cjoc202006032 Previous Articles Next Articles

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二苯并噻吩的合成研究进展

程辉成^a, 郭鹏虎^a, 陈冰^a, 姚嘉伟^a, 马姣丽^a^,^*(), 胡炜杰^a, 纪红兵^a^,^b^,^*()

a 广东石油化工学院化学学院广东高校果蔬加工与贮藏工程技术开发中心广东茂名 525000
b 中山大学化学学院精细化工研究院广州 510275

收稿日期:2020-06-18 修回日期:2020-07-26 发布日期:2020-08-19
通讯作者: 马姣丽, 纪红兵
作者简介:
* Corresponding author. E-mail: xiaojiaoli.good@163.com; jihb@mail.sysu.edu.cn
基金资助:
国家自然科学基金(21938001); 国家自然科学基金(21961160741); 茂名市科技计划(2019401); 茂名市科技计划(2020581); 广东石油化工学院基金(2012gczxB001); 广东石油化工学院基金(517152); 广东石油化工学院基金(517136); 广东石油化工学院基金(2019rc053); 广东石油化工学院基金(2019rc047)

Recent Advances in the Synthesis of Dibenzothiophenes

Huicheng Cheng^a, Penghu Guo^a, Bing Chen^a, Jiawei Yao^a, Jiaoli Ma^a^,^*(), Weijie Hu^a, Hongbing Ji^a^,^b^,^*()

a Development Center of Technology for Fruit & Vegetables Storage and Processing Engineering, College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000
b Fine Chemical Industry Research Institute, School of Chemistry, Sun Yat-sen University, Guangzhou 510275

Received:2020-06-18 Revised:2020-07-26 Published:2020-08-19
Contact: Jiaoli Ma, Hongbing Ji
Supported by:
the National Natural Science Foundation of China(21938001); the National Natural Science Foundation of China(21961160741); the Science and Technology Plan of Maoming City(2019401); the Science and Technology Plan of Maoming City(2020581); the Guangdong University of Petrochemical Technology(2012gczxB001); the Guangdong University of Petrochemical Technology(517152); the Guangdong University of Petrochemical Technology(517136); the Guangdong University of Petrochemical Technology(2019rc053); the Guangdong University of Petrochemical Technology(2019rc047)

Dibenzothiophenes are widely used in organic photoactive compounds, dyes, liquid crystals, conducting polymers, pharmaceuticals and other fields. Until now, various approaches for their synthesis have been well-documented, among which the cyclization of the C—S bond and the C—C bond to achieve the construction of a five-membered sulfur heterocycle in the dibenzothiophene structure is most widely reported. Besides, it also can be realized by the formation of a benzene ring in a dibenzothiophene structure through cyclization of thiophene/its derivatives and a four-carbon synthon. The formation of intramolecular C—S bonds by acids, bases and other non-metallic species is another alternative for dibenzothiophenes synthesis. However, most of these methods are limited by their reliance on prefunctionalization of starting materials or multistep procedures. Over the past decades, transition-metal-catalyzed coupling reactions have emerged as a powerful method for the construction of dibenzothiophenes. In this mini review, based on the latest research progress on dibenzothiophene synthesis until 2020, we briefly discuss the following types of cyclization methods.

Key words: S-heterocyclic compound, dibenzothiophenes, synthesis, transition metal catalysis, transition-metal-free

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Huicheng Cheng, Penghu Guo, Bing Chen, Jiawei Yao, Jiaoli Ma, Weijie Hu, Hongbing Ji. Recent Advances in the Synthesis of Dibenzothiophenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 94-104.

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Fig. & Tab. 32

. Representative of benzo-fused thiophenes as pharmaceuticals and organic electronics

Figure 2. Means in the construction of dibenzothiophene

Scheme 1. Anionic cyclization of benzyne-tethered aryllithiums for dibenzothiophenes

Scheme 2. Ring-closure for synthesis of dibenzothiophenes

Scheme 3. Intramolecular C—S coupling cyclization of biphenyl thioether esters for dibenzothiophenes synthesis

Scheme 4. Radical/anion-mediated sulfur-iodine exchange for dibenzothiophenes synthesis

Figure 3. Proposed mechanism for radical/anion-mediated sulfur-iodine exchange

Scheme 5. Acid-mediated intramolecular cyclization of biaryl methyl sulfoxides for dibenzothiophenes

Scheme 6. Iodine-mediated cyclization of 2-biarylyl disulfides for dibenzothiophenes

. Figure 4 Proposed reaction pathway for iodine-mediated cyclization

Scheme 7. Cu-catalyzed Ullmann reaction for synthesis of di- benzothiophenes

Scheme 8. Preparation of dibenzothiophene by Pd-catalyzed cleavage of C—S and C—H bonds

Figure 5. Proposed mechanism for Pd-catalyzed C—H/C—S coupling

Scheme 9. Cu-catalyzed dual C(aryl)—S bond formation with cyclic diaryliodoniums for dibenzothiophenes

Figure 6. Proposed mechanism for Cu sulfur-iodine exchange with cyclic diaryliodoniums

Scheme 10. Cu or Fe-catalyzed sulfur-iodine exchange for synthesis of dibenzothiophenes

Scheme 11. Pd-catalyzed tandem reaction for the synthesis of dibenzothiophenes

Scheme 12. Palladium(II)-catalyzed synthesis of dibenzothiophenes from 2-biphenylyl disulfides by C—H functionalization

Figure 7. Proposed mechanism for palladium-catalyzed C—H activation for dibenzothiophenes

Scheme 13. Pd-catalyzed cyclization of 2-biphenylthiols to di- benzothiophenes

Scheme 14. Pd-catalyzed C—S cyclization via C—H functionalization for dibenzothiophenes

Scheme 15. Palladium-catalyzed double C—H activation directed by sulfoxides for dibenzothiophenes

Figure 8. Proposed mechanism for palladium-catalyzed double C—H bond activation for dibenzothiophenes

Scheme 16. Pd-catalyzed C—S coupling and intramolecular C—H bond activation for dibenzothiophenes

Scheme 17. Palladium-catalyzed the ring closure of 2-iodized diaryl sulfide for dibenzothiophenes

Scheme 18. Pd-catalyzed intramolecular oxidative C—H/C—H coupling of diaryl sulfides to construct dibenzothiophenes

Figure 9. Proposed mechanism for palladium-catalyzed intramolecular oxidative C—H/C—H coupling for dibenzothiophenes

Scheme 19. Rh-catalyzed sequential dehydrogenation/deoxyge- nation for dibenzothiophenes

Figure 10. Proposed mechanism for Rh-catalyzed sequential dehydrogenation/deoxygenation for dibenzothiophenes

Scheme 20. Synthesis of dibenzothiophene by Lewis acid/ Bro?nsted acid mediated benz-annulation of thiophenes

Scheme 21. Synthesis of dibenzothiophene by polar Diels-Alder reactions

Scheme 22. Synthesis of dibenzothiophenes via allylic phosphonium salt initiated domino reactions

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二苯并噻吩的合成研究进展

Recent Advances in the Synthesis of Dibenzothiophenes

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