硅基羧酸在有机合成中的应用进展

doi:10.6023/cjoc202303030

摘要/Abstract

羧酸在有机体基本生命过程中起着非常重要的作用, 同时在有机合成化学领域也是一种功能强大的合成砌块. 因此, 无论是天然存在还是人工合成的羧酸都已经从多个方面被广泛研究. 硅基羧酸, 作为羧酸的类似物, 因其独特的理化性质和潜在的反应性吸引了化学家们的关注. 综述了硅基羧酸在插羰偶联反应、硅自由基反应以及酯化反应中的应用. 硅基羧酸作为硅自由基前体。

关键词: 硅基羧酸, 一氧化碳, 羰基化反应, 硅基自由基前体

Carboxylic acids play important roles in basic life processes within organisms, and are powerful building blocks in the field of organic synthesis. Therefore, natural or artificial carboxylic acids have been studied from a variety of viewpoints. Silyl carboxylic acids, as analogues of carboxylic acids, are highly attractive due to their unique physical and chemical properties as well as their potential reactivity. The applications of silyl carboxylic acids in the carbonyl coupling reactions, silyl radical reactions and esterification are summarized.

Key words: silyl carboxylic acid, carbon monoxide, carbonylation reaction, silyl radical precursor

引用此文

郭广青, 练仲. 硅基羧酸在有机合成中的应用进展[J]. 有机化学, 2023, 43(10): 3580-3589.

Guangqing Guo, Zhong Lian. Application Progress of Silyl Carboxylic Acid in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3580-3589.

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图/表 21

图式1. 硅基羧酸在有机合成化学中的应用

Scheme 1. Applications of silyl carboxylic acid in the organic synthesis chemistry

图式2. 硅基羧酸的发现与合成

Scheme 2. Discovery and synthesis of silicic acid

图式3. 硅基羧酸释放CO的机理

Scheme 3. Mechanism of CO release from silicic acid

图式4. 硅基羧酸作为CO前体的插羰反应

Scheme 4. Carbonylation reactions using silicic acid as a CO precursor

图式5. 利用芳基卤代物和硅基羧酸合成芳香羧酸

Scheme 5. Synthesis of aromatic carboxylic acids from aryl halides and silicic acids

图式6. 利用芳基卤代物和硅基羧酸合成酰胺

Scheme 6. Synthesis of amides from aryl halides and silicic acid

图式7. 芳基卤代物或烯基卤代烃的羰化反应

Scheme 7. Carbonylation coupling of aryl halides/vinyl halides

图式8. 利用2-碘苯胺和硅基羧酸合成靛红

Scheme 8. Synthesis of indigoidin from 2-iodoaniline with silicic acid

图式9. 利用芳基碘代物、氨基酸/肽亲核试剂和硅基羧酸合成酰胺

Scheme 9. Synthesis of amides from the reaction between silicic acid, aryl iodide and amino acid/peptide nucleophile

图式10. 利用烷基锌试剂、脂肪胺和硅基羧酸合成酰胺

Scheme 10. Synthesis of amides from the reaction between alkyl zinc reagents, fatty amines and silicic acid

图式11. 硅基羧酸参与的烯烃氢甲酰化反应

Scheme 11. Alkene hydroacylation reaction involving silicic acid

图式12. 硅基羧酸释放CO合成放射性药物分子

Scheme 12. Synthesis of radioactive drug molecules with CO released from silicic acid

图式13. 硅基羧酸释放CO用于示踪剂的合成

Scheme 13. Tracer synthesis with CO released from silicic acid

图式14. 硅基羧酸释放CO与Pd(II)络合物合成示踪剂

Scheme 14. Synthesis of tracer with CO released from silicic acid and Pd(II) complex

图式15. α,α-二甲基苄胺用于示踪剂的合成

Scheme 15. Tracer synthesis by using α,α-dimethylbenzylamine

图式16. 硅基羧酸用于二芳基酮的合成

Scheme 16. Synthesis of diaryl ketones with silicic acid

图式17. 硅基羧酸用于合成吲哚酮

Scheme 17. Synthesis of indolone with silicic acid

图式18. 硅基羧酸用于合成Fe配合物

Scheme 18. Synthesis of iron complexes with silicic acid

图式19. 硅基羧酸用于烯烃的氢-硅化反应

Scheme 19. Silicic acid used for the bifunctionalization of olefin

图式20. 硅基羧酸与醇的酯化反应

Scheme 20. Esterification of silicic acid with alcohol

图式21. 硅基羧酸与芳基碘代物的偶联反应

Scheme 21. Esterification of silicic acid with aryl iodide

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