C-3 Functionalization of 2-Aryl-2H-indazoles under Photo/Electrocatalysis

doi:10.6023/cjoc202208039

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 4024-4036.DOI: 10.6023/cjoc202208039 Previous Articles Next Articles

Special Issue: 自由基化学专辑

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光/电催化下2-芳基-2H-吲唑C-3位的官能团化反应

王丹凤^a, 汪瑾^a, 马春华^a^,^*(), 姜玉钦^a^,^*(), 於兵^b^,^*()

a 河南师范大学化学化工学院河南新乡 453007
b 郑州大学化学学院郑州 450001

收稿日期:2022-08-28 修回日期:2022-10-13 发布日期:2022-11-07
通讯作者: 马春华, 姜玉钦, 於兵
基金资助:
国家自然科学基金(82003585); 国家自然科学基金(21971224); 河南师范大学优秀科技创新团队(2022TD03); 中国国家级大学生创新创业训练计划(202210476076)

C-3 Functionalization of 2-Aryl-2H-indazoles under Photo/Electrocatalysis

Danfeng Wang^a, Jin Wang^a, Chunhua Ma^a(), Yuqin Jiang^a(), Bing Yu^b()

a School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
b College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2022-08-28 Revised:2022-10-13 Published:2022-11-07
Contact: Chunhua Ma, Yuqin Jiang, Bing Yu
Supported by:
National Natural Science Foundation of China(82003585); National Natural Science Foundation of China(21971224); Technical Innovation Team of Henan Normal University(2022TD03); National College Students’ Innovation and Entrepreneurship Training Program of China(202210476076)

2H-Indazole is a privileged scaffold widely existing in drugs and bioactive molecules. The C—H functionalization of 2H-indazole is the cutting edge in medicinal chemistry and organic chemistry. Compared with traditional synthetic methods, the visible light/electrochemical-promoted synthetic method has mild conditions and is an environmentally friendly synthetic strategy. The C—H functionalization of 2-aryl-2H-indazoles at the C-3 position catalyzed by photochemical/electrochemical strategies in recent years is summarized in terms of catalytic systems, with special emphasis on the corresponding reaction mechanism, which might inspire the further development of new catalytic methods.

Key words: 2H-indazole, functionalization, photocatalysis, electrocatalysis

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Danfeng Wang, Jin Wang, Chunhua Ma, Yuqin Jiang, Bing Yu. C-3 Functionalization of 2-Aryl-2H-indazoles under Photo/Electrocatalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4024-4036.

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Fig. & Tab. 17

Figure 1. Bioactive compounds with 2H-indazole scaffold

Scheme 1. C3-Phosphonylation of 2H-indazoles

Scheme 2. C3-Oxyalkylation of 2H-indazoles

Scheme 3. C3-Trifluoromethylation of 2H-indazoles

Scheme 4. C3-Amination of 2H-indazoles

Scheme 5. C3-Alkoxylation of 2H-indazoles

Scheme 6. C3-Arylation of 2H-indazoles

Scheme 7. 4CzIPN-catalyzed C3-arylation of 2H-indazoles

Scheme 8. C3-Alkylation of 2H-indazoles

Scheme 9. C3-Arylation of 2H-indazoles

Scheme 10. C3-Ethoxycarbonylmethylation of 2H-indazoles

Scheme 11. C3-Arylation of 2H-indazoles enabled by the EDA system

Scheme 12. Electrochemical C3-sulfonylation of 2H-indazoles

Scheme 13. C3-Sulfonylation of 2H-indazoles using sulfonyl hydrazides

Scheme 14. Electrochemical C3-amination of 2H-indazoles

Scheme 15. C3-Trifluoromethylation of 2H-indazoles

Scheme 16. C3-Selenylation of 2H-indazoles

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光/电催化下2-芳基-2H-吲唑C-3位的官能团化反应

C-3 Functionalization of 2-Aryl-2H-indazoles under Photo/Electrocatalysis

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