Visible light-promoted aerobic oxidative cleavage and cyclization of olefins to access 3-hydroxy-isoindolinones

Tao Ma; Jiawei Hua; Mixue Bian; Hong Qin; Xinxin Lin; Xiaobing Yang; Chengkou Liu; Zhao Yang; Zheng Fang; Kai Guo

doi:10.1039/d1qo01087e

Visible light-promoted aerobic oxidative cleavage and cyclization of olefins to access 3-hydroxy-isoindolinones

Tao Ma, Jiawei Hua, Mixue Bian, Hong Qin, Xinxin Lin, Xiaobing Yang, Chengkou Liu, Zhao Yang, Zheng Fang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

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

10 Scopus citations

Abstract

A convenient and environmentally friendly synthetic route from 2-vinylbenzimide to 3-hydroxy-isoindolinones through visible light-promoted transformations via iron/disulfide catalysis and molecular oxygen oxidation has been developed. A range of 3-hydroxy-isoindolinones was obtained in moderate to good yields, which exhibit excellent functional group compatibility and broad substrate scope. Further mechanistic investigations proved that dioxetane might be a key intermediate being involved in the reaction.

Original language	English
Pages (from-to)	25-31
Number of pages	7
Journal	Organic Chemistry Frontiers
Volume	9
Issue number	1
DOIs	https://doi.org/10.1039/d1qo01087e
State	Published - 7 Jan 2022

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abstract = "A convenient and environmentally friendly synthetic route from 2-vinylbenzimide to 3-hydroxy-isoindolinones through visible light-promoted transformations via iron/disulfide catalysis and molecular oxygen oxidation has been developed. A range of 3-hydroxy-isoindolinones was obtained in moderate to good yields, which exhibit excellent functional group compatibility and broad substrate scope. Further mechanistic investigations proved that dioxetane might be a key intermediate being involved in the reaction.",

author = "Tao Ma and Jiawei Hua and Mixue Bian and Hong Qin and Xinxin Lin and Xiaobing Yang and Chengkou Liu and Zhao Yang and Zheng Fang and Kai Guo",

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T1 - Visible light-promoted aerobic oxidative cleavage and cyclization of olefins to access 3-hydroxy-isoindolinones

AU - Ma, Tao

AU - Hua, Jiawei

AU - Bian, Mixue

AU - Qin, Hong

AU - Lin, Xinxin

AU - Yang, Xiaobing

AU - Liu, Chengkou

AU - Yang, Zhao

AU - Fang, Zheng

AU - Guo, Kai

PY - 2022/1/7

Y1 - 2022/1/7

N2 - A convenient and environmentally friendly synthetic route from 2-vinylbenzimide to 3-hydroxy-isoindolinones through visible light-promoted transformations via iron/disulfide catalysis and molecular oxygen oxidation has been developed. A range of 3-hydroxy-isoindolinones was obtained in moderate to good yields, which exhibit excellent functional group compatibility and broad substrate scope. Further mechanistic investigations proved that dioxetane might be a key intermediate being involved in the reaction.

AB - A convenient and environmentally friendly synthetic route from 2-vinylbenzimide to 3-hydroxy-isoindolinones through visible light-promoted transformations via iron/disulfide catalysis and molecular oxygen oxidation has been developed. A range of 3-hydroxy-isoindolinones was obtained in moderate to good yields, which exhibit excellent functional group compatibility and broad substrate scope. Further mechanistic investigations proved that dioxetane might be a key intermediate being involved in the reaction.

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U2 - 10.1039/d1qo01087e

DO - 10.1039/d1qo01087e

M3 - 文章

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SN - 2052-4110

VL - 9

SP - 25

EP - 31

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 1

ER -

Visible light-promoted aerobic oxidative cleavage and cyclization of olefins to access 3-hydroxy-isoindolinones

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