羧酸脱羧羟基化反应研究进展

doi:10.6023/cjoc202306005

摘要/Abstract

羧酸是廉价易得、稳定性好且功能多样的分子, 羧酸脱羧羟基化提供了从稳定易得的羧酸原料通过良性单碳切除还原直接快速获得重要醇分子的途径, 醇类化合物作为重要功能性分子在各领域的应用随处可见, 因此在有机合成和自然界中是一种非常重要和有用的转化. 主要从过渡金属催化、光催化、电催化及其他类型催化方面, 分类总结了脱羧羟基化反应得到相应伯醇、仲醇和叔醇的研究进展, 并探讨了部分反应可能的机理和适用范围. 其中过渡金属催化出现较早, 生成叔醇产率较高, 但底物普适性不强, 而光催化反应条件温和, 环境污染小, 对生成伯仲叔醇均适用.

关键词: 羧酸, 脱羧羟基化, 醇, 过渡金属催化, 光催化

Carboxylic acids are inexpensive, readily available, stable and functionally diverse molecules, and alcohols are used as important functional molecules in a variety of applications. Therefore, decarboxylative hydroxylation of carboxylic acid provides a direct and rapid route to important alcohol molecules from stabilized and easily obtainable carboxylic acid feedstocks through benign single carbon excision reductions, which is a very important and useful transformation in organic synthesis and nature. The research progress on decarboxylative hydroxylation reactions to obtain the corresponding primary, secondary and tertiary alcohols, mainly in terms of transition metal catalysis, photocatalysis, electrocatalysis and other types of catalysis, is highlighted with an emphasis on the possible mechanisms and applicable scope of these different reactions. Among them, transition metal catalysis emerged earlier and produced tertiary alcohols in higher yields, but with less universal substrates, whereas photocatalysis is a mild reaction with low environmental pollution and is suitable for the production of primary, secondary and tertiary alcohols.

Key words: carboxylic acid, decarboxylation and hydroxylation, alcohol, transition metal catalysis, photocatalysis

引用此文

赵红琼, 于淼, 宋冬雪, 贾琦, 刘颖杰, 季宇彬, 许颖. 羧酸脱羧羟基化反应研究进展[J]. 有机化学, 2024, 44(1): 70-84.

Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.

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图/表 23

图式1. 锰(III)催化新戊酸与氧气的氧化脱羧及反应机理

Scheme 1. Oxidative decarboxylation and mechanism of pivalic acid with oxygen catalyzed by Mn(III)

图式2. 银(II)催化羧酸的氧化脱羧及反应机理

Scheme 2. Silver(II) catalyzed oxidative decarboxylation and mechanism of carboxylic acids

图式3. 铈(IV)催化取代苯乙酸的氧化脱羧反应

Scheme 3. Cerium(IV) catalyzed oxidative decarboxylation of substituted phenylacetic acids

图式4. 铁卟啉-碘代苯体系催化α-芳基羧酸的氧化脱羧反应

Scheme 4. Oxidative decarboxylation of α-aryl carboxylic acids catalyzed by iron porphyrin-iodosylbenzene system

图式5. MIII(tpp)Cl/Bu4NIO4催化α-芳基羧酸的氧化脱羧反应

Scheme 5. Oxidative decarboxylation of α-aryl carboxylic acids catalyzed by MIII(tpp)Cl/Bu4NIO4

图式6. 锰(III)萨洛芬复合物催化羧酸与高碘酸钠的氧化脱羧反应

Scheme 6. Oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by Mn(III)-salophen

图式7. [Mn(NH2TPP)-CMP]催化羧酸与高碘酸钠的氧化脱羧反应

Scheme 7. Oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by [Mn(NH2TPP)-CMP]

图式8. CAN介导的N-芳基-γ-内酰胺羧酸的脱羧羟基化及反应机理

Scheme 8. CAN mediated decarboxylative hydroxylation and mechanism of N-aryl-γ-lactam-carboxylic acids

图式9. 苄基醇的合成及反应机理

Scheme 9. Synthesis of benzyl alcohols and its reaction mechanism

图式10. AgNO3/K2S2O8介导的羧酸脱羧硝基化和羟基化及反应机理

Scheme 10. AgNO3/K2S2O8-mediated decarboxylative nitration and hydroxylation and mechanism of carboxylic acids

图式11. 羧酸铈(IV)催化新戊酸的脱羧氧化反应

Scheme 11. Decarboxylative oxygenation of pivalic acids catalyzed by cerium(IV) carboxylate

图式12. 羧酸与N-羟基吡啶-2-硫酮的脱羧羟基化及反应机理

Scheme 12. Decarboxylative hydroxylation and mechanism of carboxylic acids with N-hydroxypyridine-2-thione

图式13. 吖啶介导的游离羧酸脱羧光氧化反应及反应机理

Scheme 13. Decarboxylative photooxygenation and mechanism of free carboxylic acids mediated by acridine

图式14. 羧酸与N-羟基-4-甲基-2-噻唑烷硫酮的可见光诱导脱羧羟基化反应

Scheme 14. Visible light-induced decarboxylative hydroxylation of carboxylic acids with N-hydroxy-4-methylthiazolidine-2-thione

图式15. 分子氧和MesAcrClO4催化剂介导羧酸的光催化脱羧羟基化及反应机理

Scheme 15. Photocatalytic decarboxylative hydroxylation and mechanism of carboxylic acid mediated by catalyst MesAcrClO4 and molecular oxygen

图式16. 光氧化还原催化下芳基乙酸的脱羧氧化及反应机理

Scheme 16. Decarboxylative oxidation and mechanism of arylacetic acids under photoredox catalysis

图式17. 光氧化还原催化下脂肪醇的合成及反应机理

Scheme 17. Synthesis and reaction mechanism of aliphatic alcohol under photoredox catalysis

图式18. 羧酸铈(IV)催化羧酸的脱羧氧化及反应机理

Scheme 18. Decarboxylative oxygenation and mechanism of carboxylic acids catalyzed by cerium(IV) carboxylate

图式19. 不同的sp3杂化含碳羧酸的光催化脱羧羟基化反应

Scheme 19. Photocatalytic decarboxylative hydroxylation of different sp3 carbon-bearing carboxylic acids

图式20. 以水为亲核试剂的苄基羧酸脱羧羟基化及反应机理

Scheme 20. Decarboxylative hydroxylation and mechanism of benzylic carboxylic acids with water as nucleophilea

图式21. 电催化羧酸的脱羧羟基化及反应机理

Scheme 21. Electrocatalyzed decarboxylative hydroxylation and mechanism of carboxylic acids

图式22. α-氨基酸的氧化脱羧-β-碘化及反应机理

Scheme 22. Oxidative decarboxylation-β-iodination and mechanism of α-amino acids

图式23. 水杨酸羟化酶介导的脱羧羟基化及反应机理

Scheme 23. Decarboxylative hydroxylation and mechanism mediated by salicylate hydroxylase

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