UV-Light-Initiated Construction of Indenones through Cyclization of Aryl Aldehydes or Aryl Ketones with Alkynes Avoiding Photocatalyst

doi:10.6023/cjoc202107021

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4808-4814.DOI: 10.6023/cjoc202107021 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；绿色合成化学专辑；热点论文虚拟合集

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无光催化剂条件下紫外光引发芳基醛或芳基酮与炔烃环化反应构筑茚酮化合物

肖玉娟^a, 杨阳^a, 张凡^b, 冯亚栋^a^,^b^,^*(), 崔秀灵^b^,^*()

a 厦门华厦学院环境与公共健康学院检测技术和智能仪器研究所厦门 361024
b 华侨大学生物医学学院分子药物教育部工程研究中心福建省分子医学重点实验室福建省高校精准医学与分子诊断重点实验室厦门市海洋与基因药物重点实验室厦门 361021

收稿日期:2021-07-07 修回日期:2021-07-29 发布日期:2021-08-09
通讯作者: 冯亚栋, 崔秀灵
基金资助:
福建省中青年教师教育科研(JAT190990)

UV-Light-Initiated Construction of Indenones through Cyclization of Aryl Aldehydes or Aryl Ketones with Alkynes Avoiding Photocatalyst

Yujuan Xiao^a, Yang Yang^a, Fan Zhang^b, Yadong Feng^a^,^b(), Xiuling Cui^b()

a College of Environment and Public Health, Institute of Analytical Technology and Smart Instruments, Xiamen Huaxia University, Xiamen 361024
b Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen 361021

Received:2021-07-07 Revised:2021-07-29 Published:2021-08-09
Contact: Yadong Feng, Xiuling Cui
Supported by:
Fujian Education and Scientific Research Project for Young and Middle-aged Teachers(JAT190990)

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Abstract

The first UV-light-initiated cyclization of aryl aldehydes or aryl ketones with alkynes has been developed for the preparation of indenones. This reaction could proceed smoothly under UV-light with O₂ as an oxidant and photocatalyst-free condition, which features high efficiency, high atom economy, easily available starting materials, environmental friendliness, and tolerance to broad functional groups.

Key words: UV-light, cyclization, photocatalyst-free, indenones

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Yujuan Xiao, Yang Yang, Fan Zhang, Yadong Feng, Xiuling Cui. UV-Light-Initiated Construction of Indenones through Cyclization of Aryl Aldehydes or Aryl Ketones with Alkynes Avoiding Photocatalyst[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4808-4814.

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References 21

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无光催化剂条件下紫外光引发芳基醛或芳基酮与炔烃环化反应构筑茚酮化合物

UV-Light-Initiated Construction of Indenones through Cyclization of Aryl Aldehydes or Aryl Ketones with Alkynes Avoiding Photocatalyst

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Entry	UV-light (λ_max, P)	Solvent	Temp./℃	t/h	Yield^b/%
1	365 nm, 250 W	CH₃CN	120	24	41
2	—	CH₃CN	120	24	Trace
3^c	365 nm, 250 W	CH₃CN	120	24	23
4^d	365 nm, 250 W	CH₃CN	120	24	Trace
5	365 nm, 200 W	CH₃CN	120	24	25
6	365 nm, 150 W	CH₃CN	120	24	13
7	365 nm, 250 W	CH₃OH	120	24	Nd
8	365 nm, 250 W	EtOH	120	24	Nd
9	365 nm, 250 W	DCE	120	24	11
10	365 nm, 250 W	DMF	120	24	Trace
11	365 nm, 250 W	DMSO	120	24	Nd
12	365 nm, 250 W	Toluene	120	24	20
13	365 nm, 250 W	CH₃CN	110	24	30
14	365 nm, 250 W	CH₃CN	130	24	57
15	365 nm, 250 W	CH₃CN	140	24	63
16	365 nm, 250 W	CH₃CN	150	24	60
17	365 nm, 250 W	CH₃CN	140	32	69
18	365 nm, 250 W	CH₃CN	140	40	75
19	365 nm, 250 W	CH₃CN	140	48	82
20	365 nm, 250 W	CH₃CN	140	56	73
21	365 nm, 250 W	CH₃CN	140	72	74
22^e	365 nm, 250 W	CH₃CN	140	48	28
23^f	365 nm, 250 W	CH₃CN	140	48	Trace

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