Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides

doi:10.6023/cjoc202010027

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1551-1562.DOI: 10.6023/cjoc202010027 Previous Articles Next Articles

Special Issue: 镍催化有机反应虚拟合辑

ARTICLES

镍催化的卤代糖苷和卤代芳烃通过还原偶联制备芳香碳糖苷类化合物的简易方法

孙雨人^a, 刘建东^a, 林泉^a, 姚建^a, 童玮琦^b, 钱群^b^,^*()

a 上海大学材料科学与工程学院上海大学超分子化学与催化研究中心上海 200444
b 上海大学理学院上海 200444

收稿日期:2020-10-20 修回日期:2020-11-12 发布日期:2020-12-05
通讯作者: 钱群
基金资助:
国家自然科学基金(21871173)

Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides

Yuren Sun^a, Jiandong Liu^a, Quan Lin^a, Ken Yao^a, Weiqi Tong^b, Qun Qian^b^,^*()

a School of Materials Science and Engineering, Center for Supramolecular Chemistry and Catalysis, Shanghai 200444
b College of Sciences, Shanghai University, Shanghai 200444

Received:2020-10-20 Revised:2020-11-12 Published:2020-12-05
Contact: Qun Qian
About author:
* Corresponding author. E-mail: qianqun@shu.edu.cn
Supported by:
National Natural Science Foundation of China(21871173)

1. cjoc202010027辅助材料.pdf(7281KB)

Abstract

The preparation of C-aryl glycosides via mild Ni/bipyridine-catalyzed reductive arylation of C(1)-glycosyl halides with electron-deficient aryl bromides was developed. Moderate to high α-selectivities were achieved for C-glycosides. A broad range of aryl halides including electron-rich aryl iodides were employed to yield C-aryl glycosides in 40%~5% yields. This method can be scaled up on a gram scale by lowering the loading of nickel catalyst to 2 mol%.

Key words: nickel-catalysis, reductive coupling, α-selective preparation, C-aryl glycoside, gram scale

Cite this article

Yuren Sun, Jiandong Liu, Quan Lin, Ken Yao, Weiqi Tong, Qun Qian. Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1551-1562.

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Fig. & Tab. 6

References 18

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Entry^a	Variation from the “standard conditions”	Yield^b/% (α∶β)
1	None	95 (2.2∶1)^c
2	1.5 equiv. of 2	98 (2.2∶1)
3	Ni(acac)₂ instead	70 (2∶1)
4	NiBr₂ instead	80 (2.2∶1)
5	L1b instead of L1a	85 (1.6∶1)
6	L2 instead of L1a	ND^d
7	L3 instead of L1a	Trace
8	L4 instead of L1a	ND^d
9	0 ℃	95 (2.2∶1)
10	40 ℃	93 (2∶1)
11	THF as solvent	76 (2∶1)
12	Without L1a	ND^d
13	Without MgCl₂	ND^d
14	Without MgCl₂, Ni(cod)₂ was used	85 (2.2∶1)
15	Without Zn	ND^d
16	DMA as solvent	36 (2.8∶1)
17	Without Ni(ClO₄)₂?6H₂O	ND^d

Entry^a	Variation from the “standard conditions”	Yield^b/% (α∶β)
1	None	95 (2.2∶1)^c
2	1.5 equiv. of 2	98 (2.2∶1)
3	Ni(acac)₂ instead	70 (2∶1)
4	NiBr₂ instead	80 (2.2∶1)
5	L1b instead of L1a	85 (1.6∶1)
6	L2 instead of L1a	ND^d
7	L3 instead of L1a	Trace
8	L4 instead of L1a	ND^d
9	0 ℃	95 (2.2∶1)
10	40 ℃	93 (2∶1)
11	THF as solvent	76 (2∶1)
12	Without L1a	ND^d
13	Without MgCl₂	ND^d
14	Without MgCl₂, Ni(cod)₂ was used	85 (2.2∶1)
15	Without Zn	ND^d
16	DMA as solvent	36 (2.8∶1)
17	Without Ni(ClO₄)₂?6H₂O	ND^d

镍催化的卤代糖苷和卤代芳烃通过还原偶联制备芳香碳糖苷类化合物的简易方法

Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides

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