Rhodium Catalyzed Insertion Reaction of Diazothiooxindoles for Construction of Benzothiophene Derivatives

doi:10.6023/cjoc202411013

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2501-2508.DOI: 10.6023/cjoc202411013 Previous Articles Next Articles

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铑催化硫代重氮氧化吲哚的插入反应构建苯并噻吩衍生物

崔效源^a^,^*(), 靳芳^a, 黄鑫^a, 秦涛^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:2024-11-14 修回日期:2025-01-04 发布日期:2025-02-14
基金资助:
晋中学院博士专项基金资助项目

Rhodium Catalyzed Insertion Reaction of Diazothiooxindoles for Construction of Benzothiophene Derivatives

Xiaoyuan Cui^a^,^*(), Fang Jin^a, Xin Huang^a, Tao Qin^a, Congbin Ji^b^,^*()

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

Received:2024-11-14 Revised:2025-01-04 Published:2025-02-14
Contact: *E-mail: 19121715136@163.com; jcbpxh521@163.com
Supported by:
Project supported by the Jinzhong University Research Funds for Doctor

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Abstract

Multi-substituted benzothiophene skeleton is an important synthetic intermediate, and the insertion reaction of diazo compounds catalyzed by transition metals provides a practical method for the synthesis of such compounds. This article uses Rhodium as catalyst to achieve the insertion reaction between diazothiooxindoles and pyridine carbonate compounds, providing a series of multi substituted benzothiophene compounds with good yield. This reaction has the characteristics of mild conditions and practical efficiency. At the same time, biological activity tests were conducted on several cell lines using the product, including NIH-3T3, B16-F10, 4T1 and HCT116.

Key words: multi-substituted benzothiophene, diazo compounds, metal catalysis

Cite this article

Xiaoyuan Cui, Fang Jin, Xin Huang, Tao Qin, Congbin Ji. Rhodium Catalyzed Insertion Reaction of Diazothiooxindoles for Construction of Benzothiophene Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2501-2508.

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Fig. & Tab. 6

References 15

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Entry	Catalyst	Solvent	Temp./℃	Yield^a/%
1	Ph₃PAuOTf	DCM	50	8
2	Fe(OTf)₃	DCM	50	nr
3	AgOTf	DCM	50	6
4	Cu(OTf)₂	DCM	50	nr
5	Rh₂(OAc)₄	DCM	50	68
6	Rh₂(esp)₂	DCM	50	75
7	Rh₂(esp)₂	DCM	50	70
8	Rh₂(esp)₂	DCE	50	84
9	Rh₂(esp)₂	Toluene	50	22
10	Rh₂(esp)₂	EtOAc	50	30
11	Rh₂(esp)₂	THF	50	21
12	Rh₂(esp)₂	DCE	40	74
13	Rh₂(esp)₂	DCE	60	79

Entry	Catalyst	Solvent	Temp./℃	Yield^a/%
1	Ph₃PAuOTf	DCM	50	8
2	Fe(OTf)₃	DCM	50	nr
3	AgOTf	DCM	50	6
4	Cu(OTf)₂	DCM	50	nr
5	Rh₂(OAc)₄	DCM	50	68
6	Rh₂(esp)₂	DCM	50	75
7	Rh₂(esp)₂	DCM	50	70
8	Rh₂(esp)₂	DCE	50	84
9	Rh₂(esp)₂	Toluene	50	22
10	Rh₂(esp)₂	EtOAc	50	30
11	Rh₂(esp)₂	THF	50	21
12	Rh₂(esp)₂	DCE	40	74
13	Rh₂(esp)₂	DCE	60	79

铑催化硫代重氮氧化吲哚的插入反应构建苯并噻吩衍生物

Rhodium Catalyzed Insertion Reaction of Diazothiooxindoles for Construction of Benzothiophene Derivatives

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