Rhodium-Catalyzed C—H Bond Insertion Reaction of Diazothiooxindoles with Indoles

doi:10.6023/cjoc202604022

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (10): 4016-4022.DOI: 10.6023/cjoc202604022 Previous Articles Next Articles

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铑催化的硫代重氮氧化吲哚与吲哚的碳-氢键插入反应

崔效源^a^,^*(), 闫宇慧^a, 宋毅彤^a, 石艺^a, 李雪^a, 牛慧^a, 计从斌^b^,^*()

^a 晋中学院化学化工系山西晋中 030619
^b 上饶师范学院化学与环境科学学院江西上饶 334001

收稿日期:2026-04-15 修回日期:2026-05-21 发布日期:2026-07-06
通讯作者: 崔效源, 计从斌
基金资助:
晋中学院博士专项基金、大学生创新训练计划(20251419); 山西省新型多功能玻璃技术创新中心资助项目

Rhodium-Catalyzed C—H Bond Insertion Reaction of Diazothiooxindoles with Indoles

Xiaoyuan Cui^a^,^*(), Yuhui Yan^a, Yitong Song^a, Yi Shi^a, Xue Li^a, Hui Niu^a, Congbin Ji^b^,^*()

^a Department of Chemistry & Chemical Engineering, Jinzhong University, Jinzhong, Shanxi 030619
^b School of Chemistry and Environmental Sciences, Shangrao Normal College, Shangrao, Jiangxi 334001

Received:2026-04-15 Revised:2026-05-21 Published:2026-07-06
Contact: Xiaoyuan Cui, Congbin Ji
Supported by:
Jinzhong University Research Funds for Doctor, the Undergraduate Innovation Training Program(20251419); Shanxi Province New Multi-functional Glass Technology Innovation Center

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Abstract

Thiooxindole is a very important heterocyclic skeleton, which is widely found in natural products and pharmaceutical molecules. Thiooxindole derivatives were synthesized using diazothiooxindoles and indoles as raw materials under catalysis of rhodium acetate. This reaction delivers excellent regioselectivity, affording predominantly the C(3)-selective C—H insertion products. The activities of products were tested against NIH-3T3, B16-F10, 4T1, and HCT116. The results showed that the product exhibited a certain degree of antitumor activity. This reaction system features easy operation and high atom economy.

Key words: C—H bond insertion, rhodium acetate, thiooxindole

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Xiaoyuan Cui, Yuhui Yan, Yitong Song, Yi Shi, Xue Li, Hui Niu, Congbin Ji. Rhodium-Catalyzed C—H Bond Insertion Reaction of Diazothiooxindoles with Indoles[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 4016-4022.

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References 18

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Entry	Catalyst	Solvent	T/℃	Yield^a/%
1	Ph₃PAuOTf	CH₂Cl₂	50	20
2	Fe(OTf)₃	CH₂Cl₂	50	10
3	AgOTf	CH₂Cl₂	50	8
4	Cu(OTf)₂	CH₂Cl₂	50	15
5	Rh₂(OAc)₄	CH₂Cl₂	50	72
6	Rh₂(OAc)₄	CHCl₃	50	70
7	Rh₂(OAc)₄	DCE	50	79
8	Rh₂(OAc)₄	Toluene	50	23
9	Rh₂(OAc)₄	EtOAc	50	28
10	Rh₂(OAc)₄	THF	50	37
11	Rh₂(OAc)₄	DCE	40	73
12	Rh₂(OAc)₄	DCE	60	75

Entry	Catalyst	Solvent	T/℃	Yield^a/%
1	Ph₃PAuOTf	CH₂Cl₂	50	20
2	Fe(OTf)₃	CH₂Cl₂	50	10
3	AgOTf	CH₂Cl₂	50	8
4	Cu(OTf)₂	CH₂Cl₂	50	15
5	Rh₂(OAc)₄	CH₂Cl₂	50	72
6	Rh₂(OAc)₄	CHCl₃	50	70
7	Rh₂(OAc)₄	DCE	50	79
8	Rh₂(OAc)₄	Toluene	50	23
9	Rh₂(OAc)₄	EtOAc	50	28
10	Rh₂(OAc)₄	THF	50	37
11	Rh₂(OAc)₄	DCE	40	73
12	Rh₂(OAc)₄	DCE	60	75

铑催化的硫代重氮氧化吲哚与吲哚的碳-氢键插入反应

Rhodium-Catalyzed C—H Bond Insertion Reaction of Diazothiooxindoles with Indoles

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