Cyclization and Coupling Reactions Promoted by Potassium tert-Butoxide

doi:10.6023/cjoc202203029

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 1950-1959.DOI: 10.6023/cjoc202203029 Previous Articles Next Articles

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叔丁醇钾促进的环化和偶联反应

张力之, 廖永剑, 陈宁, 黄磊, 周敏^*()

云南民族大学民族医药学院昆明 650031

收稿日期:2022-03-15 修回日期:2022-04-19 发布日期:2022-08-09
通讯作者: 周敏
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(32060101); 云南省优秀青年基金(202001AW070002); 云南省万人计划(YNWR-QNBJ-2019-206); 云南省中青年学术带头人后备人才(2019HB016)

Cyclization and Coupling Reactions Promoted by Potassium tert-Butoxide

Lizhi Zhang, Yongjian Liao, Ning Chen, Lei Huang, Min Zhou()

School of Ethnic Medicine, Yunnan Minzu University, Kunming 650031

Received:2022-03-15 Revised:2022-04-19 Published:2022-08-09
Contact: Min Zhou
About author:
^†These authors contribute equally to this work
Supported by:
National Natural Science Foundation of China(32060101); Yunnan Applied Basic Research Projects for Excellent Young Scholars(202001AW070002); Yunnan Ten Thousand Talents Program(YNWR-QNBJ-2019-206); Candidates of the Young and Middle Aged Academic Leaders of Yunnan Province(2019HB016)

Over the past few decades, transition metal-catalyzed reactions have been developed into a powerful tool for building various chemical bonds. At the same time, non-metal-promoted chemical bond construction reactions have attracted more and more attention of synthetic chemists because of the avoiding of using expensive metal catalysts and ligands, resulting in the reduce of reaction costs and environmental pollution. It conforms to the concept of green chemistry development. Among them, potassium tert-butoxide-promoted cyclization and coupling reactions have been rapidly developed. The intramolecular cyclization and intermolecular coupling reactions involving potassium tert-butoxide since 2000 are summarized, and the possible reaction mechanisms are elucidated, which can help chemists better understand the development of this field and promote the development of this field.

Key words: potassium t-butoxide, intramolecular cyclization, free radical reaction, coupling reaction

Cite this article

Lizhi Zhang, Yongjian Liao, Ning Chen, Lei Huang, Min Zhou. Cyclization and Coupling Reactions Promoted by Potassium tert-Butoxide[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1950-1959.

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Fig. & Tab. 27

Scheme 1. Intramolecular cyclization of allylamine and ketone promoted by KOtBu

Scheme 2. Intramolecular cyclization of allyl ethers and ketones promoted by KOtBu

Scheme 3. Mechanism of the intramolecular cyclization reaction between allylamine and ketone promoted by KOtBu

Scheme 4. Intramolecular cyclization of tetrahydroisoquinoline derivatives

Scheme 5. Verification experiment of the intramolecular cyclization mechanism of tetrahydroisoquinoline derivatives

Scheme 6. Chemoselective cyclization

Scheme 7. Deprotonation-cyclization-dehydration process of domino

Scheme 8. KOtBu catalyzes the cyclization of alkynyl alcohol

Scheme 9. KOtBu catalyzes the cyclization of alkynamine

Scheme 10. Cyclization reaction mechanism of alkynol or alkynamine catalyzed by KOtBu

Scheme 11. Gilson synthesis of benzodiazepine

Scheme 12. Mechanism of Gilsonʼs synthesis of benzodiazepines

Scheme 13. Intramolecular cyclization of alkenyl iodide promoted by KOtBu and bipyridine

Scheme 14. Aromatization in substituted aromatics

Scheme 15. Synthesis mechanism of 2-acetylbenzofuran

Scheme 16. Cross-coupling of aryl bromide and phenol

Scheme 17. Cross-coupling of benzene and o-chlorobenzaldehyde

Scheme 18. Synthesis of benzothiazole from 2-aminothiophenol

Scheme 19. Oxidative coupling of olefins and aldehydes, TBHP and KOtBu

Scheme 20. Oxidative coupling mechanism

Scheme 21. Biaryl coupling promoted by KOtBu

Scheme 22. Cross-coupling of benzaldehyde and indole

Scheme 23. Control experiment for the synthesis of bis(indolyl)arylmethane

Scheme 24. Direct aromatization of unactivated aromatics catalyzed by DMEDA

Scheme25. Cross-coupling of aryl iodide and aromatic hydrocarbon

Scheme 26. Synthesis of 2-alkylazaarene

Scheme 27. Phenanthroline and KOtBu as precursors of electron donors

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叔丁醇钾促进的环化和偶联反应

Cyclization and Coupling Reactions Promoted by Potassium tert-Butoxide

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