α-酮酸在无金属有机光合成中的应用

doi:10.6023/cjoc202109008

摘要/Abstract

α-酮酸作为一种羧酸, 可以通过脱羧作用, 作为酰基化试剂应用于有机合成, 但是传统方法往往依赖过渡金属催化剂或高温等反应条件, 在一定程度上限制了其应用. 近年来发展的可见光诱导的有机反应由于条件温和及易于操作等优点而受到广泛关注. 综述了无金属条件下可见光诱导的α-酮酸的相关反应研究进展, 主要包括在酰基化反应和环化反应中的应用.

关键词: α-酮酸, 可见光, 无金属催化, 酰基化

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

引用此文

谢坤宸, 江铭轩, 陈晓岚, 吕琪妍, 於兵. α-酮酸在无金属有机光合成中的应用[J]. 有机化学, 2021, 41(12): 4575-4587.

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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图/表 30

图1. α-酮酸及其脱羧反应中的有机光催化剂的结构

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

图式1. 日光促进下由炔溴和α-酮酸合成炔酮

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

图式2. 可见光照射下合成C(3)-位酰化吲哚

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

图式3. 合成C(3)-位酰化吲哚的反应机理

Scheme 3. Mechanism of synthesis of 3-acylindoles

图式4. 可见光催化下草氨酸和醇脱羧偶联制备氨基甲酸酯

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

图式5. 可见光催化下合成非对称脲

Scheme 5. Visible-light photocatalyzed synthesis of unsymmetrical ureas

图式6. 可见光催化下草氨酸氧化脱羧反应机理

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

图式7. 可见光促进异腈、α-酮酸和水三组分合成α-酮酰胺

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

图式8. 可见光促进下合成C(3)位-酰化喹喔啉-2(1H)-酮

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

图式9. 合成C(3)位-酰化喹喔啉-2(1H)-酮的反应机理

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

图式10. 可见光促进下α-酮酸对偶氮苯的氢化酰化

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

图式11. 可见光促进下α-酮酸与卤代芳烃偶联合成酮

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

图式12. 可见光促进下合成C(4)-位酰化喹啉

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

图式13. 可见光下合成C(4)-位酰化喹啉的反应机理

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

图式14. 可见光下氮杂环与α-酮酸的脱羧酰化反应

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

图式15. 可见光诱导下喹喔啉-2(1H)-酮的无光敏剂酰化反应

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

图式16. 可见光下喹喔啉-2(1H)-酮的酰化反应机理

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

图式17. 可见光诱导下由2-氨基苯硫酚和α-酮酸合成苯并噻唑

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

图式18. 可见光诱导下合成苯并噻唑的机理

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

图式19. 可见光促进下合成异喹啉1,3-(2H,4H)二酮

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

图式20. 合成异喹啉1,3-(2H,4H)二酮的反应机理

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

图式21. 可见光下4CzIPN催化的无金属杂环酰化反应

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

图式22. 4CzIPN催化的酰化/环化反应机理

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

图式23. 可见光下无光敏剂合成氧化吲哚类化合物

Scheme 23. Synthesis of oxindoles under visible light without photosensitizer

图式24. 可见光下合成羟吲哚类化合物的机理

Scheme 24. Mechanism of synthesis of oxindoles under visible light

图式25. 光化学合成3-羟基菲-[9,10-c]并呋喃-1(3H)-酮及其衍生物

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

图式26. 光化学合成3-羟基菲-[9,10-c]并呋喃-1(3H)-酮的机理

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

图式27. 可见光催化下由乙烯基环丁醇与α-酮酸合成1,4-二羰基化合物

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

图式28. 可见光促进下草氨酸对氮杂环的自由基加成反应

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

图式29. 由草氨酸和含氮杂环合成手性酰胺

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

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