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

doi:10.6023/cjoc202010027

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1551-1562.DOI: 10.6023/cjoc202010027 上一篇下一篇

所属专题：镍催化有机反应虚拟合辑

研究论文

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)

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摘要/Abstract

报道了在温和条件下通过镍和联吡啶催化的还原偶联反应, 由C(1)-卤代糖苷和缺电子的芳基溴化物制备芳香糖苷类化合物的方法. 运用该种方法可以由中等或高的α-选择性得到芳香碳糖苷类产物. 包括富电子的芳香碘化物在内的多种卤代芳烃底物适用于该反应, 产率在40%~95%之间. 该方法可以放大到克级规模, 并在此条件下将镍催化剂的用量减少到2 mol%.

关键词: 镍催化, 还原偶联, α-选择性制备, 芳香碳糖苷, 克级反应

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

引用此文

孙雨人, 刘建东, 林泉, 姚建, 童玮琦, 钱群. 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[J]. 有机化学, 2021, 41(4): 1551-1562.

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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参考文献 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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