A Metal-free Approach to 3-Aryl-3-hydroxy-2-oxindoles by Treatment of 3-Acyloxy-2-oxindoles with Diaryliodonium Salts

Xiaokang Li; Wei Ni; Fei Mao; Wei Wang; Jian Li

doi:10.1002/asia.201500854

A Metal-free Approach to 3-Aryl-3-hydroxy-2-oxindoles by Treatment of 3-Acyloxy-2-oxindoles with Diaryliodonium Salts

Xiaokang Li, Wei Ni, Fei Mao, Wei Wang, Jian Li

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

10 Scopus citations

Abstract

A mild, metal-free approach has been realized for the facile construction of highly valuable 3-(hetero)aryl-3-hydroxy-2-oxindoles. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K₂CO₃ at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields. A new family member: A simple and efficient method for direct arylation of 3-acyloxy-2-oxindoles has been developed. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K₂CO₃ at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields.

Original language	English (US)
Pages (from-to)	226-230
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	2
DOIs	https://doi.org/10.1002/asia.201500854
State	Published - Jan 20 2016
Externally published	Yes

Keywords

3-acyloxy-2-oxindoles
3-aryl-3-hydroxy-2-oxindole
arylation
diaryliodonium salt
metal-free

ASJC Scopus subject areas

General Chemistry
Biochemistry
Organic Chemistry

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10.1002/asia.201500854

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title = "A Metal-free Approach to 3-Aryl-3-hydroxy-2-oxindoles by Treatment of 3-Acyloxy-2-oxindoles with Diaryliodonium Salts",

abstract = "A mild, metal-free approach has been realized for the facile construction of highly valuable 3-(hetero)aryl-3-hydroxy-2-oxindoles. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K2CO3 at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields. A new family member: A simple and efficient method for direct arylation of 3-acyloxy-2-oxindoles has been developed. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K2CO3 at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields.",

keywords = "3-acyloxy-2-oxindoles, 3-aryl-3-hydroxy-2-oxindole, arylation, diaryliodonium salt, metal-free",

author = "Xiaokang Li and Wei Ni and Fei Mao and Wei Wang and Jian Li",

note = "Funding Information: Financial support of this research provided by the National Natural Science Foundation of China (Grants 21222211, 21372001, 91313303 and 21372073), the Program for New Century Excellent Talents in University (Grant NCET-12-0853), {"}Shu Guang{"} project supported by Shanghai Municipal Education Commission and Shanghai Education Development Foundation (Grant 14SG28), and the Fundamental Research Funds for the Central Universities is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

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doi = "10.1002/asia.201500854",

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AU - Li, Xiaokang

AU - Ni, Wei

AU - Mao, Fei

AU - Wang, Wei

AU - Li, Jian

N1 - Funding Information: Financial support of this research provided by the National Natural Science Foundation of China (Grants 21222211, 21372001, 91313303 and 21372073), the Program for New Century Excellent Talents in University (Grant NCET-12-0853), "Shu Guang" project supported by Shanghai Municipal Education Commission and Shanghai Education Development Foundation (Grant 14SG28), and the Fundamental Research Funds for the Central Universities is gratefully acknowledged. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2016/1/20

Y1 - 2016/1/20

N2 - A mild, metal-free approach has been realized for the facile construction of highly valuable 3-(hetero)aryl-3-hydroxy-2-oxindoles. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K2CO3 at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields. A new family member: A simple and efficient method for direct arylation of 3-acyloxy-2-oxindoles has been developed. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K2CO3 at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields.

AB - A mild, metal-free approach has been realized for the facile construction of highly valuable 3-(hetero)aryl-3-hydroxy-2-oxindoles. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K2CO3 at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields. A new family member: A simple and efficient method for direct arylation of 3-acyloxy-2-oxindoles has been developed. Direct arylations of 3-acyloxy-2-oxindoles with diaryliodonium salts as arylation reagents are implemented in the presence of K2CO3 at room temperature without using an organometallic promoter to deliver an array of 3-(hetero)aryl-3-hydroxy-2-oxindoles in good yields.

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KW - arylation

KW - diaryliodonium salt

KW - metal-free

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A Metal-free Approach to 3-Aryl-3-hydroxy-2-oxindoles by Treatment of 3-Acyloxy-2-oxindoles with Diaryliodonium Salts

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