Visible-Light-Induced C—C Bond Cleavage of Dihydroquinazolinones with Trifluoromethyl-Substituted Olefins Defluorinated Alkylation Reactions

doi:10.6023/cjoc202311028

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1549-1557.DOI: 10.6023/cjoc202311028 Previous Articles Next Articles

ARTICLES

可见光诱导二氢喹唑啉酮碳碳键断裂与三氟甲基取代烯烃的脱氟烷基化反应研究

曹香雪^b, 贾雅会^b, 殷世纪^b, 徐亮^b, 韦玉^b^,^*(), 宋欢欢^a^,^*()

a 石河子大学兵团能源发展研究院新疆石河子 832003
b 石河子大学化学化工学院化工绿色过程省部共建国家重点实验室培育基地新疆石河子 832003

收稿日期:2023-11-26 修回日期:2024-01-24 发布日期:2024-02-07
基金资助:
国家自然科学基金(22061036); 国家自然科学基金(21963010)

Visible-Light-Induced C—C Bond Cleavage of Dihydroquinazolinones with Trifluoromethyl-Substituted Olefins Defluorinated Alkylation Reactions

Xiangxue Cao^b, Yahui Jia^b, Shiji Yin^b, Liang Xu^b, Yu Wei^b(), Huanhuan Song^a()

a Bingtuan Energy Development Institute, Shihezi University, Shihezi, Xinjiang 832003
b State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2023-11-26 Revised:2024-01-24 Published:2024-02-07
Contact: *E-mail: yuweichem@shzu.edu.cn; songhh@shzu.edu.cn
Supported by:
National Natural Science Foundation of China(22061036); National Natural Science Foundation of China(21963010)

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Abstract

The visible-light-induced C—C bond cleavage of dihydroquinazolinone to generate alkyl radicals for defluorinated alkylation reactions with α-trifluoromethyl alkene is reported. The method is featured as transition-metal-free, mild conditions, base- or additive-free, and has a wide range of substrate applicability, which provides a convenient and efficient new method for the synthesis of various alkyl-substituted gem-difluoroalkene.

Key words: visible-light catalysis, dihydroquinazolinone, C—C bond cleavage, gem-difluoroalkene, α-trifluoromethyl alkene

Cite this article

Xiangxue Cao, Yahui Jia, Shiji Yin, Liang Xu, Yu Wei, Huanhuan Song. Visible-Light-Induced C—C Bond Cleavage of Dihydroquinazolinones with Trifluoromethyl-Substituted Olefins Defluorinated Alkylation Reactions[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1549-1557.

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Fig. & Tab. 5

References 21

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Entry	Variations from the standard condition	Yield^b/%
1	None	80
2	Without 4CzIPN	N.R.^c
3	Without light	N.R.^c
4	Air instead of Ar	Trace
5	AQDAB instead of 4CzIPN	40
6	DMF (1.0 mL) instead of DMSO (1.0 mL)	60
7	NMP (1.0 mL) instead of DMSO (1.0 mL)	30
8	MeCN (1.0 mL) instead of DMSO (1.0 mL)	Trace
9	MeOH (1.0 mL) instead of DMSO (1.0 mL)	Trace
10	EA (1.0 mL) instead of DMSO (1.0 mL)	N.R.^c
11	THF (1.0 mL) instead of DMSO (1.0 mL)	Trace
12	DCM (1.0 mL) instead of DMSO (1.0 mL)	N.R.^c
13	MTBE (1.0 mL) instead of DMSO (1.0 mL)	N.R.^c
14	455 nm blue LEDs instead of 450 nm blue LEDs	74

Entry	Variations from the standard condition	Yield^b/%
1	None	80
2	Without 4CzIPN	N.R.^c
3	Without light	N.R.^c
4	Air instead of Ar	Trace
5	AQDAB instead of 4CzIPN	40
6	DMF (1.0 mL) instead of DMSO (1.0 mL)	60
7	NMP (1.0 mL) instead of DMSO (1.0 mL)	30
8	MeCN (1.0 mL) instead of DMSO (1.0 mL)	Trace
9	MeOH (1.0 mL) instead of DMSO (1.0 mL)	Trace
10	EA (1.0 mL) instead of DMSO (1.0 mL)	N.R.^c
11	THF (1.0 mL) instead of DMSO (1.0 mL)	Trace
12	DCM (1.0 mL) instead of DMSO (1.0 mL)	N.R.^c
13	MTBE (1.0 mL) instead of DMSO (1.0 mL)	N.R.^c
14	455 nm blue LEDs instead of 450 nm blue LEDs	74

可见光诱导二氢喹唑啉酮碳碳键断裂与三氟甲基取代烯烃的脱氟烷基化反应研究

Visible-Light-Induced C—C Bond Cleavage of Dihydroquinazolinones with Trifluoromethyl-Substituted Olefins Defluorinated Alkylation Reactions

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References 21

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