Photoredox-Catalzyed Halo-trifluoromethylation of 1,7-Enynes for Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

Xin Yuan; Ming Wei Zheng; Zhe Chen Di; Yu Sheng Cui; Kai Qiang Zhuang; Long Zhou Qin; Zheng Fang; Jiang Kai Qiu; Guigen Li; Kai Guo

doi:10.1002/adsc.201801681

Photoredox-Catalzyed Halo-trifluoromethylation of 1,7-Enynes for Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

Xin Yuan, Ming Wei Zheng, Zhe Chen Di, Yu Sheng Cui, Kai Qiang Zhuang, Long Zhou Qin, Zheng Fang, Jiang Kai Qiu, Guigen Li, Kai Guo

Chemistry and Biochemistry

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

16 Scopus citations

Abstract

An efficient photoredox-catalyzed halo-trifluoromethylation reaction of 1,7-enynes has been developed under mild conditions. This photocatalytic protocol provides an efficient and functional strategy leading to CF ₃ − and halogen-containing 3,4-dihydroquinolin-2(1H)-ones from a wide range of 1,7-enynes through two different radical pathways. The reaction mechanism was proposed based on the control experiments. (Figure presented.).

Original language	English
Pages (from-to)	1835-1845
Number of pages	11
Journal	Advanced Synthesis and Catalysis
Volume	361
Issue number	8
DOIs	https://doi.org/10.1002/adsc.201801681
State	Published - Apr 16 2019

Keywords

1,7-enynes
halo-trifluoromethylation
photoredox
radical pathway

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title = "Photoredox-Catalzyed Halo-trifluoromethylation of 1,7-Enynes for Synthesis of 3,4-Dihydroquinolin-2(1H)-ones",

abstract = " An efficient photoredox-catalyzed halo-trifluoromethylation reaction of 1,7-enynes has been developed under mild conditions. This photocatalytic protocol provides an efficient and functional strategy leading to CF 3 − and halogen-containing 3,4-dihydroquinolin-2(1H)-ones from a wide range of 1,7-enynes through two different radical pathways. The reaction mechanism was proposed based on the control experiments. (Figure presented.). ",

keywords = "1,7-enynes, halo-trifluoromethylation, photoredox, radical pathway",

author = "Xin Yuan and Zheng, {Ming Wei} and Di, {Zhe Chen} and Cui, {Yu Sheng} and Zhuang, {Kai Qiang} and Qin, {Long Zhou} and Zheng Fang and Qiu, {Jiang Kai} and Guigen Li and Kai Guo",

note = "Funding Information: We are grateful for financial support from the National Natural Science Foundation of China (Grant No. 21702103, 21522604, U1463201 and 21402240) and the Youth in Jiangsu Province Natural Science Fund (Grant No. BK20150031, BK20130913 and BY2014005-03). Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = apr,

day = "16",

doi = "10.1002/adsc.201801681",

language = "English",

volume = "361",

pages = "1835--1845",

journal = "Advanced Synthesis and Catalysis",

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Photoredox-Catalzyed Halo-trifluoromethylation of 1,7-Enynes for Synthesis of 3,4-Dihydroquinolin-2(1H)-ones. / Yuan, Xin; Zheng, Ming Wei; Di, Zhe Chen; Cui, Yu Sheng; Zhuang, Kai Qiang; Qin, Long Zhou; Fang, Zheng; Qiu, Jiang Kai; Li, Guigen; Guo, Kai.

In: Advanced Synthesis and Catalysis, Vol. 361, No. 8, 16.04.2019, p. 1835-1845.

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

TY - JOUR

T1 - Photoredox-Catalzyed Halo-trifluoromethylation of 1,7-Enynes for Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

AU - Yuan, Xin

AU - Zheng, Ming Wei

AU - Di, Zhe Chen

AU - Cui, Yu Sheng

AU - Zhuang, Kai Qiang

AU - Qin, Long Zhou

AU - Fang, Zheng

AU - Qiu, Jiang Kai

AU - Li, Guigen

AU - Guo, Kai

N1 - Funding Information: We are grateful for financial support from the National Natural Science Foundation of China (Grant No. 21702103, 21522604, U1463201 and 21402240) and the Youth in Jiangsu Province Natural Science Fund (Grant No. BK20150031, BK20130913 and BY2014005-03). Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/4/16

Y1 - 2019/4/16

N2 - An efficient photoredox-catalyzed halo-trifluoromethylation reaction of 1,7-enynes has been developed under mild conditions. This photocatalytic protocol provides an efficient and functional strategy leading to CF 3 − and halogen-containing 3,4-dihydroquinolin-2(1H)-ones from a wide range of 1,7-enynes through two different radical pathways. The reaction mechanism was proposed based on the control experiments. (Figure presented.).

AB - An efficient photoredox-catalyzed halo-trifluoromethylation reaction of 1,7-enynes has been developed under mild conditions. This photocatalytic protocol provides an efficient and functional strategy leading to CF 3 − and halogen-containing 3,4-dihydroquinolin-2(1H)-ones from a wide range of 1,7-enynes through two different radical pathways. The reaction mechanism was proposed based on the control experiments. (Figure presented.).

KW - 1,7-enynes

KW - halo-trifluoromethylation

KW - photoredox

KW - radical pathway

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JO - Advanced Synthesis and Catalysis

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SN - 1615-4150

IS - 8

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Photoredox-Catalzyed Halo-trifluoromethylation of 1,7-Enynes for Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

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