Application of α-Keto Acids in Metal-Free Photocatalysis

doi:10.6023/cjoc202109008

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4575-4587.DOI: 10.6023/cjoc202109008 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；绿色合成化学专辑；热点论文虚拟合集

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α-酮酸在无金属有机光合成中的应用

谢坤宸, 江铭轩, 陈晓岚, 吕琪妍^*(), 於兵^*()

郑州大学化学学院绿色催化中心郑州 450001

收稿日期:2021-09-04 修回日期:2021-10-13 发布日期:2021-10-20
通讯作者: 吕琪妍, 於兵
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21971224); 国家自然科学基金(22171249); 大学生创新创业训练计划(S202110459196); 大学生创新创业训练计划(2021cxcy197); 郑州大学本科生拔尖计划资助项目

Application of α-Keto Acids in Metal-Free Photocatalysis

Kunchen Xie, Mingxuan Jiang, Xiaolan Chen, Qiyan Lü(), Bing Yu()

College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2021-09-04 Revised:2021-10-13 Published:2021-10-20
Contact: Qiyan Lü, Bing Yu
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21971224); National Natural Science Foundation of China(22171249); Innovation and Entrepreneurship Training Program(S202110459196); Innovation and Entrepreneurship Training Program(2021cxcy197); Top Undergraduates Program of Zhengzhou University

As a carboxylic acid, α-keto acid can be used as an acylating reagent by decarboxylation in organic synthesis. However, traditional methods often need transition metal catalysts or high temperatures, which limits the application of α-keto acid to a certain extent. In recent years, organic transformations induced by visible light have attracted extensive attention due to its mild conditions and simple operations. Herein, the recent advances of metal-free photocatalytic application of α-keto acids are summarized, which mainly include acylation reactions and cyclization reactions.

Key words: α-keto acid, visible light, metal-free catalysis, acylation

Cite this article

Kunchen Xie, Mingxuan Jiang, Xiaolan Chen, Qiyan Lü, Bing Yu. Application of α-Keto Acids in Metal-Free Photocatalysis[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4575-4587.

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Fig. & Tab. 30

Figure 1. Structures of α-keto acid and organophotocatalyst for its decarboxylation

Scheme 1. Sunlight-driven synthesis of ynones from α-keto acids and bromoacetylenes

Scheme 2. Synthesis of 3-acylindoles under visible light irradiation

Scheme 3. Mechanism of synthesis of 3-acylindoles

Scheme 4. Synthesis of urethanes by photocatalytic decarboxylation coupling of oxamic acids and alcohols

Scheme 5. Visible-light photocatalyzed synthesis of unsymmetrical ureas

Scheme 6. Mechanism of visible-light photocatalyzed oxidative decarboxylation of oxamic acids

Scheme 7. Synthesis of α-ketoamides with isocyanides, α-oxocarboxylic acids and water

Scheme 8. Visible-light promoted synthesis of 3-acylquinoxaline-2(1H)-ones

Scheme 9. Mechanism of synthesis of 3-acylquinoxaline-2(1H)-ones

Scheme 10. Hydroacylation of azobenzenes by α-keto acids under visible-light

Scheme 11. Visible-light promoted coupling reaction of α -keto acids and aromatic halides

Scheme 12. Visible-light promoted synthesis of C(4)-acyl-quinolines

Scheme 13. Mechanism of synthesis of 4-acylquinoline under visible-light

Scheme 14. Visible light-induced decarboxylative acylation of N-heterocycles and α-keto acids

Scheme 15. Visible-light-induced acylation of quinoxalin- 2(1H)-ones without photocatalyst

Scheme 16. Mechanism of acylation of quinoxalin-2(1H)-ones under visible-light

Scheme 17. Visible-light-induced synthesis of benzothiazoles from α-keto acids and 2-aminothiophenol

Scheme 18. Mechanism of visible-light-induced synthesis of benzothiazoles

Scheme 19. Visible light-promoted synthesis of isoquinoline- 1,3(2H,4H)-dione

Scheme 20. Mechanism of synthesis of isoquinoline-1,3- (2H,4H)-dione

Scheme 21. Metal-free acylation of heterocycles catalyzed by 4CzIPN under visible-light

Scheme 22. Mechanism of acylation/cyclization catalyzed by 4CzIPN

Scheme 23. Synthesis of oxindoles under visible light without photosensitizer

Scheme 24. Mechanism of synthesis of oxindoles under visible light

Scheme 25. Photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones and its derivatives

Scheme 26. Mechanism of photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones

Scheme 27. Visible-light-catalyzed synthesis of 1,4-dicarbonyl compounds from vinylcyclobutanols and α-keto acids

Scheme 28. Visible light-promoted radical addition of oxamic acids to N-heterocycles

Scheme 29. Synthesis of chiral amides with oxamic acids and N-heterocycles compounds

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α-酮酸在无金属有机光合成中的应用

Application of α-Keto Acids in Metal-Free Photocatalysis

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