Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

Huaqiang Fan; Peng Pan; Yongqiang Zhang; Wei Wang

doi:10.1021/acs.orglett.8b03503

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

Huaqiang Fan, Peng Pan, Yongqiang Zhang, Wei Wang

Pharmacology and Toxicology

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

27 Scopus citations

Abstract

A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

Original language	English (US)
Pages (from-to)	7929-7932
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.8b03503
State	Published - Dec 21 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b03503

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title = "Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature",

abstract = "A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.",

author = "Huaqiang Fan and Peng Pan and Yongqiang Zhang and Wei Wang",

note = "Funding Information: Financial support from the program of the National Natural Science Foundation of China (21602060, 21871086, Y.-Q.Z.; 21572055, 21738002, W.W.) and the Chinese Fundamental Research Funds for the Central Universities (ECUST: WY1714033) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b03503",

language = "English (US)",

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T1 - Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

AU - Fan, Huaqiang

AU - Pan, Peng

AU - Zhang, Yongqiang

AU - Wang, Wei

N1 - Funding Information: Financial support from the program of the National Natural Science Foundation of China (21602060, 21871086, Y.-Q.Z.; 21572055, 21738002, W.W.) and the Chinese Fundamental Research Funds for the Central Universities (ECUST: WY1714033) is gratefully acknowledged. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/12/21

Y1 - 2018/12/21

N2 - A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

AB - A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

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Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

Abstract

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