2-碘酰基苯甲酸在有机合成中的研究与应用

doi:10.6023/cjoc202007030

有机化学 ›› 2021, Vol. 41 ›› Issue (2): 490-503.DOI: 10.6023/cjoc202007030 上一篇下一篇

综述与进展

2-碘酰基苯甲酸在有机合成中的研究与应用

张书瑜¹, 吴昊天¹, 汤峨¹^,^*()

1 云南大学化学科学与工程学院教育部自然资源药物化学重点实验室昆明650091

收稿日期:2020-07-09 修回日期:2020-08-11 发布日期:2020-09-16
通讯作者: 汤峨
作者简介:
* Corresponding author. E-mail: tange@ynu.edu.cn
基金资助:
长江学者和创新团队发展计划(IRT13095); 国家自然科学基金(21762046); 云南科技厅-云南大学“双一流”建设联合基金(2018FY001); 云南省高校科技创新团队支持计划及云南大学“青年英才”培育计划资助项目

Research and Application of 2-Iodoxybenzoic Acid in Organic Synthesis

Shuyu Zhang¹, Haotian Wu¹, E Tang¹^,^*()

1 Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091

Received:2020-07-09 Revised:2020-08-11 Published:2020-09-16
Contact: E Tang
Supported by:
the Program for Changjiang Scholars and Innovative Research Team in University(IRT13095); the Natural Science Foundation of China(21762046); the Program for Yunnan Provincial Department of Science and Technology-Yunnan University "Double First-Class" Construction Joint Fund(2018FY001); the Program for Scientifically and Technologically Innovative Research Teams in the Universities in Yunnan Province and the Program for the “Young Talent” in Yunnan University.

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摘要/Abstract

高价有机碘化合物的反应性质与过渡金属相似, 其参与的反应具有反应条件较温和、选择性好、产率高及环境友好等优点, 因而近年来关于高价有机碘试剂的研究受到广泛关注, 在有机合成领域中获得了较多应用. 综述了近年来高价有机碘试剂2-碘酰基苯基酸(IBX)在有机合成中的研究及应用, 包括IBX在氧化羟基、含氮化合物和含硫化合物, 在制备αβ-不饱和羰基化合物和α,β-不饱和酯, 以及在不对称合成等方面的应用. 最后介绍了近期对IBX的改进.

关键词: 2-碘酰基苯甲酸(IBX), 氧化, 有机合成, 高价有机碘

High-valent organoiodine reagents have many reaction characteristics similar to transition metals, and high-valent organoiodine-mediated reactions feature mild reaction conditions, good product selectivity, high yield and environmental friendliness. Therefore, they have been widely studied and applied in organic synthesis. The recent research progress of 2-iodoxybenzoic acid in organic synthesis is reviewed, including the oxidation of hydroxyl group, nitrogen-containing compounds and sulfur-containing compounds, the preparation of α,β-unsaturated carbonyl compounds and esters, and the application in asymmetric synthesis. The recent improvement of IBX is also introduced.

Key words: 2-iodoxybenzoic acid (IBX), oxidation, organic synthesis, high-valent organoiodine

引用此文

张书瑜, 吴昊天, 汤峨. 2-碘酰基苯甲酸在有机合成中的研究与应用[J]. 有机化学, 2021, 41(2): 490-503.

Shuyu Zhang, Haotian Wu, E Tang. Research and Application of 2-Iodoxybenzoic Acid in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 490-503.

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图/表 20

图1. IBX氧化环氧化合物反应机理

Figure 1. Mechanism of the oxidation reaction of epoxy compounds by IBX

图式1. IBX参与的2-氨基芳基酮28的串联反应

Scheme 1. IBX-mediated cascade reaction of 2-aminoaryl ketones 28

图式2. IBX氧化羟胺成肟可能的反应机理

Scheme 2. Proposed mechanism of the oxidation reaction of hydroxylamines to oximes by IBX

图式3. 苯并咪唑化合物42的合成

Scheme 3. Synthesis of benzimidazole compounds 42

图式4. 2-胺基苯并噁唑化合物49的合成

Scheme 4. Synthesis of 2-aminobenzoxazole compounds 49

图式5. 喹诺酮、萘啶酮和苯并萘啶酮化合物52的合成

Scheme 5. Synthesis of quinolone, naphthyridone and benzonaphthyridone compounds 52

图式6. IBX/NIS促进氧化环化

Scheme 6. IBX/NIS-promoted oxidation cyclization

图式7. 可能的氧化环化机理

Scheme 7. Plausible mechanism of the oxidation cyclization

图式8. α-氨基酸衍生物的合成

Scheme 8. Synthesis of α-amino acid derivatives

图式9. IBX的选择性氧化四氢萘酮

Scheme 9. Selective oxidation of 3,4-dihydronaphthalen-1(2H)- one with IBX

图式10. 吲哚啉2,3-二酮化合物93的合成

Scheme 10. Synthesis of indoline-2,3-dione 93

图式11. IBX-I2氧化α-羟基酮的可能机理

Scheme 11. A possible mechanism of the oxidation reaction of α-hydroxyketone by IBX-I 2

图式12. 反式-2-脱氧-2-碘糖基乙酸酯和邻碘苯甲酸酯的选择性合成

Scheme 12. Selective synthesis of trans-2-deoxy-2-iodoglycosylacetates and O-iodobenzoates

图式13. IBX参与的黄酮化合物的修饰

Scheme 13. IBX-mediated modification of flavonoids

图式14. 二氢吡喃氮酮衍生物的合成

Scheme 14. Synthesis of dihydropyranic azaphilone derivatives

图式15. 三组分聚合

Scheme 15. Three-component polymerization

图式16. IBX氧化法合成α-酮醛化合物

Scheme 16. Synthesis of α-ketone aldehyde via the oxidation by IBX

图式17. TetMe-IBX催化氧化α-溴代醇

Scheme 17. TetMe-IBX catalytic oxidation of α-bromoalkahol

图式18. IBX氧化吲哚制备吲哚啉-2,3-二酮

Scheme 18. Synthesis of indoline-2,3-diones via oxidation of indole by IBX

图式19. IBX氧化胺和醇的反应机理

Scheme 19. Mechanism of amine and alcohol oxidation mediated by IBX

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2-碘酰基苯甲酸在有机合成中的研究与应用

Research and Application of 2-Iodoxybenzoic Acid in Organic Synthesis

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