Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides

doi:10.6023/cjoc202110010

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4738-4748.DOI: 10.6023/cjoc202110010 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

ARTICLES

光催化下β-萘酚与二芳基膦氧化物区域选择性邻位膦酰化研究

袁金伟^a^,^*(), 刘燕^a, 葛元元^a, 董少轩^a, 宋赛依^a, 杨亮茹^a^,^*(), 肖咏梅^a, 张守仁^b^,^*(), 屈凌波^c^,^*()

a 河南工业大学化学化工学院郑州 450001
b 黄河科技学院纳米功能材料研究所郑州 450006
c 郑州大学化学学院郑州 450001

收稿日期:2021-10-09 修回日期:2021-11-09 发布日期:2021-11-17
通讯作者: 袁金伟, 杨亮茹, 张守仁, 屈凌波
基金资助:
河南省教育厅自然科学基金(21A150016); 河南工业大学创新基金支持计划专项(2020ZKCJ29); 河南工业大学省高校创新基金(2017RCJH08); 河南省高校国家大学生创新(201910463009); 河南省高校国家大学生创新(201910463013)

Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides

Jinwei Yuan^a(), Yan Liu^a, Yuanyuan Ge^a, Shaoxuan Dong^a, Saiyi Song^a, Liangru Yang^a(), Yongmei Xiao^a, Shouren Zhang^b(), Lingbo Qu^c()

a School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001
b Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006
c College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2021-10-09 Revised:2021-11-09 Published:2021-11-17
Contact: Jinwei Yuan, Liangru Yang, Shouren Zhang, Lingbo Qu
Supported by:
Natural Science Foundation in Department of Education of Henan Province(21A150016); Innovative Funds Plan of Henan University of Technology(2020ZKCJ29); Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology(2017RCJH08); National Undergraduate Innovation and Entrepreneurship Training Program from the University in Henan Province(201910463009); National Undergraduate Innovation and Entrepreneurship Training Program from the University in Henan Province(201910463013)

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Abstract

A metal-free visible-light-induced regioselective ortho-C—H phosphonylation of β-naphthols with diarylphosphine oxides has been developed using fluorescein as an organophotoredox catalyst in the presence of K₂S₂O₈ at room temperature under N₂ atmosphere. This feature along with mild reaction conditions, sensitive functional group tolerance, good to excellent yields, high regioselectivity, and scale-up synthesis makes it an ideal and practical alternative modification of β-naphthols. The experimental result suggests that a radical pathway is involved in the reaction.

Key words: β-naphthols, diarylphosphine oxide, visible-light catalysis, phosphonylation, radical reaction

Cite this article

Jinwei Yuan, Yan Liu, Yuanyuan Ge, Shaoxuan Dong, Saiyi Song, Liangru Yang, Yongmei Xiao, Shouren Zhang, Lingbo Qu. Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4738-4748.

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Entry	Catalyst (mol%)	Oxidant (equiv.)	Solvent	Time/h	Yield^b/%
1	—	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	11
2	Rhodamine B (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	0
3	Eosin Y (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	Trace
4	Eosin B (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	Trace
5	Fluorescein (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	65
6	Ruthenium (0.1)^c	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	Trace
7	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	80
8	Fluorescein (0.15)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	45
9	Fluorescein (0.2)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	40
10	Fluorescein (0.05)	(NH₄)₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	70
11	Fluorescein (0.05)	TBPB (2.0)	DMF-H₂O (V∶V=1∶1)	16	15
12	Fluorescein (0.05)	DTBP (2.0)	DMF-H₂O (V∶V=1∶1)	16	21
13	Fluorescein (0.05)	BPO (2.0)	DMF-H₂O (V∶V=1∶1)	16	26
14	Fluorescein (0.05)	K₂S₂O₈ (1.0)	DMF-H₂O (V∶V=1∶1)	16	48
15	Fluorescein (0.05)	K₂S₂O₈ (1.5)	DMF-H₂O (V∶V=1∶1)	16	67
16	Fluorescein (0.05)	K₂S₂O₈ (2.5)	DMF-H₂O (V∶V=1∶1)	16	78
17	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMSO	16	12
18	Fluorescein (0.05)	K₂S₂O₈ (2.0)	MeCN	16	25
19	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DCE	16	20
20	Fluorescein (0.05)	K₂S₂O₈ (2.0)	Dioxane	16	34
21^c	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF	16	67
22^d	Fluorescein (0.05)	K₂S₂O₈ (2.0)	H₂O	16	0
23	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	2	50
24	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	4	71
25	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	6	83
26	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	8	78
27^d	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	6	85
28^e	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	6	0
29^f	Fluorescein (0.05)	—	DMF-H₂O (V∶V=1∶1)	6	0

Entry	Catalyst (mol%)	Oxidant (equiv.)	Solvent	Time/h	Yield^b/%
1	—	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	11
2	Rhodamine B (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	0
3	Eosin Y (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	Trace
4	Eosin B (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	Trace
5	Fluorescein (0.1)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	65
6	Ruthenium (0.1)^c	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	Trace
7	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	80
8	Fluorescein (0.15)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	45
9	Fluorescein (0.2)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	40
10	Fluorescein (0.05)	(NH₄)₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	16	70
11	Fluorescein (0.05)	TBPB (2.0)	DMF-H₂O (V∶V=1∶1)	16	15
12	Fluorescein (0.05)	DTBP (2.0)	DMF-H₂O (V∶V=1∶1)	16	21
13	Fluorescein (0.05)	BPO (2.0)	DMF-H₂O (V∶V=1∶1)	16	26
14	Fluorescein (0.05)	K₂S₂O₈ (1.0)	DMF-H₂O (V∶V=1∶1)	16	48
15	Fluorescein (0.05)	K₂S₂O₈ (1.5)	DMF-H₂O (V∶V=1∶1)	16	67
16	Fluorescein (0.05)	K₂S₂O₈ (2.5)	DMF-H₂O (V∶V=1∶1)	16	78
17	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMSO	16	12
18	Fluorescein (0.05)	K₂S₂O₈ (2.0)	MeCN	16	25
19	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DCE	16	20
20	Fluorescein (0.05)	K₂S₂O₈ (2.0)	Dioxane	16	34
21^c	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF	16	67
22^d	Fluorescein (0.05)	K₂S₂O₈ (2.0)	H₂O	16	0
23	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	2	50
24	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	4	71
25	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	6	83
26	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	8	78
27^d	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	6	85
28^e	Fluorescein (0.05)	K₂S₂O₈ (2.0)	DMF-H₂O (V∶V=1∶1)	6	0
29^f	Fluorescein (0.05)	—	DMF-H₂O (V∶V=1∶1)	6	0

光催化下β-萘酚与二芳基膦氧化物区域选择性邻位膦酰化研究

Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides

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