Visible Light-Induced 4-Chromanones Synthesis: Radical Cascade Cyclization of α-Oxocarboxylic Acids with o-(Allyloxy)arylaldehydes Promoted by Phenyliodine(III) Diacetate

doi:10.6023/cjoc202204005

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2488-2495.DOI: 10.6023/cjoc202204005 Previous Articles Next Articles

ARTICLES

可见光诱导4-色满酮合成: 醋酸碘苯促进的α-酮酸与邻-烯丙氧基芳醛的自由基串联环化反应

周旭煜, 张爱君, 张庆庆, 刘庆安^*(), 宣俊^*()

安徽大学化学化工学院无机-有机杂化功能材料化学安徽省重点实验室合肥 230601

收稿日期:2022-04-03 修回日期:2022-05-02 发布日期:2022-05-17
通讯作者: 刘庆安, 宣俊
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(21971001); 国家自然科学基金(21702001); 国家级大学生创新创业计划(202110357041)

Visible Light-Induced 4-Chromanones Synthesis: Radical Cascade Cyclization of α-Oxocarboxylic Acids with o-(Allyloxy)arylaldehydes Promoted by Phenyliodine(III) Diacetate

Xuyu Zhou, Aijun Zhang, Qingqing Zhang, Qing'an Liu(), Jun Xuan()

Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei 230601

Received:2022-04-03 Revised:2022-05-02 Published:2022-05-17
Contact: Qing'an Liu, Jun Xuan
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21971001); National Natural Science Foundation of China(21702001); National Undergraduate Training Program for Innovation and Entrepreneurship(202110357041)

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Abstract

An efficient and sustainable visible light-promoted cascade radical cyclization of α-oxocarboxylic acids with o-(allyloxy)arylaldehydes towards the construction of 1,4-diketone containing chromanone derivatives has been developed. The reaction occurred under mild reactions, e.g. room temperature, blue LED irradiation, photoredox catalyst free, and provided the final heterocycles in moderate to good yields.

Key words: visible light, 4-chromanone, radical, cascade reaction

Cite this article

Xuyu Zhou, Aijun Zhang, Qingqing Zhang, Qing'an Liu, Jun Xuan. Visible Light-Induced 4-Chromanones Synthesis: Radical Cascade Cyclization of α-Oxocarboxylic Acids with o-(Allyloxy)arylaldehydes Promoted by Phenyliodine(III) Diacetate[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2488-2495.

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Entry	Deviation from standard conditions	Yield^b/%
1	None	26
2	DCE instead of CH₃CN	21
3	EtOAc instead of CH₃CN	25
4	THF instead of CH₃CN	12
5	Toluene instead of CH₃CN	9
6	DMF instead of CH₃CN	Trace
7	DMSO instead of CH₃CN	Trace
8	MeOH instead of CH₃CN	0
9	H₂O instead of CH₃CN	0
10	1a:2a=1:4, 12 h	62
11	1a:2a=1:4, 24 h	61
12^c	1a:2a=1:4, 12 h	Trace
13	Without PIDA	0
14	Without blue LEDs	0

Entry	Deviation from standard conditions	Yield^b/%
1	None	26
2	DCE instead of CH₃CN	21
3	EtOAc instead of CH₃CN	25
4	THF instead of CH₃CN	12
5	Toluene instead of CH₃CN	9
6	DMF instead of CH₃CN	Trace
7	DMSO instead of CH₃CN	Trace
8	MeOH instead of CH₃CN	0
9	H₂O instead of CH₃CN	0
10	1a:2a=1:4, 12 h	62
11	1a:2a=1:4, 24 h	61
12^c	1a:2a=1:4, 12 h	Trace
13	Without PIDA	0
14	Without blue LEDs	0

可见光诱导4-色满酮合成: 醋酸碘苯促进的α-酮酸与邻-烯丙氧基芳醛的自由基串联环化反应

Visible Light-Induced 4-Chromanones Synthesis: Radical Cascade Cyclization of α-Oxocarboxylic Acids with o-(Allyloxy)arylaldehydes Promoted by Phenyliodine(III) Diacetate

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