Copper-Catalyzed Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindolinone Derivatives

Veerababurao Kavala; Li Chun Lin; Prakash Bhimrao Patil; Chia Chi Fang; Zih Yu Hong; Yi Ru Liou; Yu Nong Chen; Yin Zhi Weng; Sundaramoorthi Sarathkumar; Naidu Sambasiva Rao; Sundaram Suresh; Zongyan Jiang; Ching Fa Yao

doi:10.1002/adsc.202200235

Copper-Catalyzed Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindolinone Derivatives

Veerababurao Kavala, Li Chun Lin, Prakash Bhimrao Patil, Chia Chi Fang, Zih Yu Hong, Yi Ru Liou, Yu Nong Chen, Yin Zhi Weng, Sundaramoorthi Sarathkumar, Naidu Sambasiva Rao, Sundaram Suresh, Zongyan Jiang, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

A one-pot strategy for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives is reported. The reaction proceeds via a copper-catalyzed oxidative cascade inter-molecular double cyclization of 2-iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The strategy involves several reactions including cyclization/coupling/double C(sp3)−H functionalization in a cascade manner. A wide range of 2-iodobenzamide substrates containing different substituents as well as various propargyldicarbonyl compounds and propargylsulfonyl aryl ketones can be used to access a variety of 3-hydroxy-3-furylisoindolinone derivatives. (Figure presented.).

Original language	English
Pages (from-to)	2801-2814
Number of pages	14
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	16
DOIs	https://doi.org/10.1002/adsc.202200235
Publication status	Published - 2022 Aug 16

Keywords

2-Iodobenzamides
3-Hydroxy-3-furylisoindolinone
Cascade
Copper
Double cyclization

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.202200235

Cite this

Kavala, V., Lin, L. C., Bhimrao Patil, P., Fang, C. C., Hong, Z. Y., Liou, Y. R., Chen, Y. N., Weng, Y. Z., Sarathkumar, S., Sambasiva Rao, N., Suresh, S., Jiang, Z., & Yao, C. F. (2022). Copper-Catalyzed Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindolinone Derivatives. Advanced Synthesis and Catalysis, 364(16), 2801-2814. https://doi.org/10.1002/adsc.202200235

Copper-Catalyzed Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindolinone Derivatives. / Kavala, Veerababurao; Lin, Li Chun; Bhimrao Patil, Prakash et al.
In: Advanced Synthesis and Catalysis, Vol. 364, No. 16, 16.08.2022, p. 2801-2814.

Research output: Contribution to journal › Article › peer-review

Kavala, V, Lin, LC, Bhimrao Patil, P, Fang, CC, Hong, ZY, Liou, YR, Chen, YN, Weng, YZ, Sarathkumar, S, Sambasiva Rao, N, Suresh, S, Jiang, Z & Yao, CF 2022, 'Copper-Catalyzed Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindolinone Derivatives', Advanced Synthesis and Catalysis, vol. 364, no. 16, pp. 2801-2814. https://doi.org/10.1002/adsc.202200235

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abstract = "A one-pot strategy for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives is reported. The reaction proceeds via a copper-catalyzed oxidative cascade inter-molecular double cyclization of 2-iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The strategy involves several reactions including cyclization/coupling/double C(sp3)−H functionalization in a cascade manner. A wide range of 2-iodobenzamide substrates containing different substituents as well as various propargyldicarbonyl compounds and propargylsulfonyl aryl ketones can be used to access a variety of 3-hydroxy-3-furylisoindolinone derivatives. (Figure presented.).",

keywords = "2-Iodobenzamides, 3-Hydroxy-3-furylisoindolinone, Cascade, Copper, Double cyclization",

author = "Veerababurao Kavala and Lin, {Li Chun} and {Bhimrao Patil}, Prakash and Fang, {Chia Chi} and Hong, {Zih Yu} and Liou, {Yi Ru} and Chen, {Yu Nong} and Weng, {Yin Zhi} and Sundaramoorthi Sarathkumar and {Sambasiva Rao}, Naidu and Sundaram Suresh and Zongyan Jiang and Yao, {Ching Fa}",

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month = aug,

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doi = "10.1002/adsc.202200235",

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AU - Kavala, Veerababurao

AU - Lin, Li Chun

AU - Bhimrao Patil, Prakash

AU - Fang, Chia Chi

AU - Hong, Zih Yu

AU - Liou, Yi Ru

AU - Chen, Yu Nong

AU - Weng, Yin Zhi

AU - Sarathkumar, Sundaramoorthi

AU - Sambasiva Rao, Naidu

AU - Suresh, Sundaram

AU - Jiang, Zongyan

AU - Yao, Ching Fa

PY - 2022/8/16

Y1 - 2022/8/16

N2 - A one-pot strategy for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives is reported. The reaction proceeds via a copper-catalyzed oxidative cascade inter-molecular double cyclization of 2-iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The strategy involves several reactions including cyclization/coupling/double C(sp3)−H functionalization in a cascade manner. A wide range of 2-iodobenzamide substrates containing different substituents as well as various propargyldicarbonyl compounds and propargylsulfonyl aryl ketones can be used to access a variety of 3-hydroxy-3-furylisoindolinone derivatives. (Figure presented.).

AB - A one-pot strategy for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives is reported. The reaction proceeds via a copper-catalyzed oxidative cascade inter-molecular double cyclization of 2-iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The strategy involves several reactions including cyclization/coupling/double C(sp3)−H functionalization in a cascade manner. A wide range of 2-iodobenzamide substrates containing different substituents as well as various propargyldicarbonyl compounds and propargylsulfonyl aryl ketones can be used to access a variety of 3-hydroxy-3-furylisoindolinone derivatives. (Figure presented.).

KW - 2-Iodobenzamides

KW - 3-Hydroxy-3-furylisoindolinone

KW - Cascade

KW - Copper

KW - Double cyclization

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Copper-Catalyzed Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindolinone Derivatives

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 2145559: Experimental Crystal Structure Determination

CCDC 2145558: Experimental Crystal Structure Determination

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Copper-Catalyzed Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3-Hydroxy-3-Furylisoindolinone Derivatives

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 2145559: Experimental Crystal Structure Determination

CCDC 2145558: Experimental Crystal Structure Determination

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