Rh(III)-Catalyzed Annulation of Azobenzenes with Vinylene Carbonate

doi:10.6023/cjoc202107038

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 172-180.DOI: 10.6023/cjoc202107038 Previous Articles Next Articles

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Rh(III)催化偶氮苯与碳酸亚乙烯基酯的环化反应

张文杰^a, 李超^a, 王博超^a, 高慧^a^,^b^,^*(), 李洪基^a^,^*()

a 淮北师范大学化学与材料科学学院教育部绿色和精准合成化学及应用重点实验室安徽淮北 235000
b 广西师范大学省部共建药用资源化学与药物分子工程国家重点实验室广西桂林 541004

收稿日期:2021-07-18 修回日期:2021-09-16 发布日期:2021-09-26
通讯作者: 高慧, 李洪基
基金资助:
国家自然科学基金(21772061); 安徽省高校优秀人才(gxyq2020015); 省部共建药用资源化学与药物分子工程国家重点实验室(广西师范大学)(CMEMR2021-B14)

Rh(III)-Catalyzed Annulation of Azobenzenes with Vinylene Carbonate

Wenjie Zhang^a, Chao Li^a, Bochao Wang^a, Hui Gao^a^,^b(), Hongji Li^a()

a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000
b State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Guangxi 541004

Received:2021-07-18 Revised:2021-09-16 Published:2021-09-26
Contact: Hui Gao, Hongji Li
Supported by:
National Natural Science Foundation of China(21772061); Research Funding for Outstanding Young Talents in Colleges and Universities of Anhui Province(gxyq2020015); State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University)(CMEMR2021-B14)

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Abstract

A mild Rh(III)-catalyzed annulation of azobenzenes with vinylene carbonate via inert C—H bond activation has been developed. In this reaction system, vinylene carbonate provides one vinyl carbon for the construction of indazole backbone, and leaves the other one for the formation of aldehyde. This annulation enables the direct synthesis of 2H-indazole- 3-carbaldehyde with excellent regioselectivity in moderate to good yields.

Key words: Rh catalysis, azobenzene, vinylene carbonate, annulation

Cite this article

Wenjie Zhang, Chao Li, Bochao Wang, Hui Gao, Hongji Li. Rh(III)-Catalyzed Annulation of Azobenzenes with Vinylene Carbonate[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 172-180.

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Entry	Catalyst	Additive	Yield^b/%
1	[Cp*RhCl₂]₂	—	n.r.
2	[Cp*RhCl₂]₂	AgSbF₆	60
3	[Cp*RhCl₂]₂	AgTFA	40
4	[Cp*RhCl₂]₂	AgOAc	72
5	[Cp*Rh(MeCN)₃](SbF₆)₂	AgOAc	67
6	[Cp*CoCl₂]₂	AgOAc	n.r.
7	[Cp*IrCl₂]₂	AgOAc	n.r.
8	[Cp*RhCl₂]₂	AgOAc	66^c
9	[Cp*RhCl₂]₂	AgOAc	71^d
10	[Cp*RhCl₂]₂	AgOAc	68^e
11	[Cp*RhCl₂]₂	AgOAc	53^f
12	[Cp*RhCl₂]₂	AgOAc	56^g
13	[Cp*RhCl₂]₂	AgOAc	62^h

Entry	Catalyst	Additive	Yield^b/%
1	[Cp*RhCl₂]₂	—	n.r.
2	[Cp*RhCl₂]₂	AgSbF₆	60
3	[Cp*RhCl₂]₂	AgTFA	40
4	[Cp*RhCl₂]₂	AgOAc	72
5	[Cp*Rh(MeCN)₃](SbF₆)₂	AgOAc	67
6	[Cp*CoCl₂]₂	AgOAc	n.r.
7	[Cp*IrCl₂]₂	AgOAc	n.r.
8	[Cp*RhCl₂]₂	AgOAc	66^c
9	[Cp*RhCl₂]₂	AgOAc	71^d
10	[Cp*RhCl₂]₂	AgOAc	68^e
11	[Cp*RhCl₂]₂	AgOAc	53^f
12	[Cp*RhCl₂]₂	AgOAc	56^g
13	[Cp*RhCl₂]₂	AgOAc	62^h

Rh(III)催化偶氮苯与碳酸亚乙烯基酯的环化反应

Rh(III)-Catalyzed Annulation of Azobenzenes with Vinylene Carbonate

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