Research and Application of 2-Iodoxybenzoic Acid in Organic Synthesis

doi:10.6023/cjoc202007030

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 490-503.DOI: 10.6023/cjoc202007030 Previous Articles Next Articles

Review

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.

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

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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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Fig. & Tab. 20

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

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

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

Scheme 3. Synthesis of benzimidazole compounds 42

Scheme 4. Synthesis of 2-aminobenzoxazole compounds 49

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

Scheme 6. IBX/NIS-promoted oxidation cyclization

Scheme 7. Plausible mechanism of the oxidation cyclization

Scheme 8. Synthesis of α-amino acid derivatives

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

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

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

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

Scheme 13. IBX-mediated modification of flavonoids

Scheme 14. Synthesis of dihydropyranic azaphilone derivatives

Scheme 15. Three-component polymerization

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

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

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

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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