Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides

doi:10.6023/cjoc202112029

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1414-1422.DOI: 10.6023/cjoc202112029 Previous Articles Next Articles

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可见光-铜共催化的糖类区域选择性氧烷基化反应

孙天义, 张依凡, 孟远倢, 王怡, 朱琦峰^*(), 姜玉新^*(), 刘石惠^*()

嘉兴学院医学院浙江嘉兴 314001

收稿日期:2021-12-22 修回日期:2022-01-18 发布日期:2022-02-27
通讯作者: 朱琦峰, 姜玉新, 刘石惠
基金资助:
国家自然科学基金青年基金(22001096); 浙江省自然科学基金(LQ21B020008); 嘉兴学院启动经费(CD70519040); 嘉兴学院“百青”培养人才(CD70621018)

Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides

Tianyi Sun, Yifan Zhang, Yuanjie Meng, Yi Wang, Qifeng Zhu(), Yuxin Jiang(), Shihui Liu()

College of Medicine, Jiaxing University, Jiaxing, Zhejiang 314001

Received:2021-12-22 Revised:2022-01-18 Published:2022-02-27
Contact: Qifeng Zhu, Yuxin Jiang, Shihui Liu
Supported by:
National Natural Science Foundation of China(22001096); Natural Science Foundation of Zhejiang Province(LQ21B020008); Start up Funds of Jiaxing University(CD70519040); Jiaxing University “Hundred Youth” Training Talents(CD70621018)

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Abstract

A photoredox-copper dual-catalyzed cross dehydrogenative coupling reaction of glycosides with benzylic C—H substrates has been developed. The reaction proceeds smoothly under mild reaction conditions and features the using of readily accessible starting materials, which allows the highly site-selective synthesis of diverse glycosides O-alkylation products in 27%~72% yields, providing a new synthetic tool for the site-selective modification of glycosides.

Key words: photoredox catalysis, copper catalysis, site-selective alkylation, glycosides

Cite this article

Tianyi Sun, Yifan Zhang, Yuanjie Meng, Yi Wang, Qifeng Zhu, Yuxin Jiang, Shihui Liu. Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1414-1422.

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References 13

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Entry	Photocatalyst	Oxidant	Metal	Ligand	Yield^a/% of 3a
1	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	Ni(acac)₂	bpy^b	55
2	[Ir(ppy)₂(dtbbpy)]PF₆	Selectfluor	Ni(acac)₂	bpy^b	29
3 ^c	4CzIPN	Selectfluor	Ni(acac)₂	bpy^b	22
4 ^d	Eosin Y	Selectfluor	Ni(acac)₂	bpy^b	n.d.^e
5	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	APS ^f	Ni(acac)₂	bpy^b	n.d.^e
6	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Oxone ^g	Ni(acac)₂	bpy^b	n.d.^e
7	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	NFSI ^h	Ni(acac₎₂	bpy^b	46
8	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	NiBr₂	bpy^b	35
9	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	bpy^b	58
10	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CoCl₂	bpy^b	n.d.^e
11	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	dtbpyⁱ	54
12	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	phen^j	46
13	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L13	64
14	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L14	52
15	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L15	57
16^k	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L13	37
17	—	Selectfluor	CuBr	L13	10
18	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	—	CuBr	L13	n.d.^e
19	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	—	L13	33
20	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	—	46
21^l	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L13	42

Entry	Photocatalyst	Oxidant	Metal	Ligand	Yield^a/% of 3a
1	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	Ni(acac)₂	bpy^b	55
2	[Ir(ppy)₂(dtbbpy)]PF₆	Selectfluor	Ni(acac)₂	bpy^b	29
3 ^c	4CzIPN	Selectfluor	Ni(acac)₂	bpy^b	22
4 ^d	Eosin Y	Selectfluor	Ni(acac)₂	bpy^b	n.d.^e
5	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	APS ^f	Ni(acac)₂	bpy^b	n.d.^e
6	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Oxone ^g	Ni(acac)₂	bpy^b	n.d.^e
7	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	NFSI ^h	Ni(acac₎₂	bpy^b	46
8	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	NiBr₂	bpy^b	35
9	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	bpy^b	58
10	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CoCl₂	bpy^b	n.d.^e
11	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	dtbpyⁱ	54
12	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	phen^j	46
13	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L13	64
14	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L14	52
15	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L15	57
16^k	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L13	37
17	—	Selectfluor	CuBr	L13	10
18	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	—	CuBr	L13	n.d.^e
19	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	—	L13	33
20	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	—	46
21^l	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	CuBr	L13	42

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可见光-铜共催化的糖类区域选择性氧烷基化反应

Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides

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