Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones

doi:10.6023/cjoc202405016

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3505-3517.DOI: 10.6023/cjoc202405016 Previous Articles Next Articles

ARTICLE

Rh(III)催化烯烃与重氮化物氨基烷基化反应构筑异吲哚啉酮

刘玉英^†,a^,^b^,^c^,^d, 符展维^†,a^,^b^,^c^,^d, 杨超^d, 罗木鹏^d^,^*(), 班树荣^a^,^b^,^c^,^*(), 王守国^d^,^*()

a 山西医科大学药学院太原 030001
b 山西医科大学慢性肾脏病教育部医药基础研究创新中心太原 030001
c 山西医科大学药物合成与制剂新技术山西省重点实验室太原 030001
d 中国科学院深圳先进技术研究院深圳 518055

收稿日期:2024-05-13 修回日期:2024-05-22 发布日期:2024-05-30
作者简介:
†共同第一作者
基金资助:
山西省自然科学基金(202303021221131); 山西省特色药物研制工程研究中心和深圳市科技创新委员会(JCYJ20210324101810028); 山西省特色药物研制工程研究中心和深圳市科技创新委员会(JCYJ-20220818101601004); 山西省特色药物研制工程研究中心和深圳市科技创新委员会(JCYJ20220818095801004)

Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones

Yuying Liu^†,a^,^b^,^c^,^d, Zhanwei Fu^†,a^,^b^,^c^,^d, Chao Yang^d, Mupeng Luo^d,*(), Shurong Ban^a^,^b^,^c,*(), Shouguo Wang^d,*()

a School of Pharmacy, Shanxi Medical University, Taiyuan 030001
b Medicinal Basic Research Innovation Center of Chronic Kidney Disease, Ministry of Education, Shanxi Medical University, Taiyuan 030001
c Shanxi Provincial Key Laboratory of Drug Synthesis and Novel Pharmaceutical Preparation Technology, Shanxi Medical University, Taiyuan 030001
d Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055

Received:2024-05-13 Revised:2024-05-22 Published:2024-05-30
Contact: *E-mail:shouguo.wang@siat.ac.cn;shurongban@sxmu.edu.cn;mp.luo@siat.ac.cn
About author:
†These authors contributed equally to this work.
Supported by:
Natural Science Foundation of Shanxi Province(202303021221131); Project of Shanxi Engineering Research Center of Characteristic Drug Development, and the Shenzhen Science and Technology Innovation Committee(JCYJ20210324101810028); Project of Shanxi Engineering Research Center of Characteristic Drug Development, and the Shenzhen Science and Technology Innovation Committee(JCYJ-20220818101601004); Project of Shanxi Engineering Research Center of Characteristic Drug Development, and the Shenzhen Science and Technology Innovation Committee(JCYJ20220818095801004)

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Abstract

A [Cp*RhCl₂]₂-catalyzed intramolecular annulation reaction via aminoalkylation of alkenes with diazo compounds has been developed to construct highly-functionalized isoindolinones. This approach exhibits step economy, mild reaction conditions, and good functional group tolerance, facilitating access to a wide range of highly-valuable functionalized isoindolinones with high level of yields (up to 99% yield).

Key words: aminoalkylation reaction, annulation reaction, isoindolinone, Rh(Ⅲ)-catalysis, diazo compounds

Cite this article

Yuying Liu, Zhanwei Fu, Chao Yang, Mupeng Luo, Shurong Ban, Shouguo Wang. Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3505-3517.

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Fig. & Tab. 7

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Entry	Variation from the standard conditions	Yield^b/%
1	None	>99 (99)^c
2	CH₃OH instead of DCE	66
3	CH₂Cl₂ instead of DCE	76
4	Toluene instead of DCE	78
5	THF instead of DCE	83
6	AgBF₄ instead of AgSbF₆	76
7	AgNTf₂ instead of AgSbF₆	78
8	AgOAc instead of AgSbF₆	64
9	40 ^oC instead of 60 ^oC	74
10	1.25 mol% [Cp*RhCl₂]₂	60
11	1.2 equiv. 2a	87
12	No AgSbF₆	NP
13	[CpIrCl₂]₂ instead of [CpRhCl₂]₂	NP

Entry	Variation from the standard conditions	Yield^b/%
1	None	>99 (99)^c
2	CH₃OH instead of DCE	66
3	CH₂Cl₂ instead of DCE	76
4	Toluene instead of DCE	78
5	THF instead of DCE	83
6	AgBF₄ instead of AgSbF₆	76
7	AgNTf₂ instead of AgSbF₆	78
8	AgOAc instead of AgSbF₆	64
9	40 ^oC instead of 60 ^oC	74
10	1.25 mol% [Cp*RhCl₂]₂	60
11	1.2 equiv. 2a	87
12	No AgSbF₆	NP
13	[CpIrCl₂]₂ instead of [CpRhCl₂]₂	NP

Rh(III)催化烯烃与重氮化物氨基烷基化反应构筑异吲哚啉酮

Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones

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