异喹啉-3-羧酸根螯合的B,B-二芳基四配位硼络合物的合成

doi:10.6023/cjoc202301001

有机化学 ›› 2023, Vol. 43 ›› Issue (5): 1792-1798.DOI: 10.6023/cjoc202301001 上一篇下一篇

所属专题：有机硼化学专辑

研究论文

异喹啉-3-羧酸根螯合的B,B-二芳基四配位硼络合物的合成

田维娜^a, 徐亮^a, 韦玉^a^,^*(), 李鹏飞^b^,^*()

a 石河子大学化学化工学院化工绿色过程省部共建国家重点实验室培育基地新疆石河子 832003
b 西安交通大学前沿科学技术研究院西安 710054

收稿日期:2023-01-02 修回日期:2023-03-01 发布日期:2023-04-13
通讯作者: 韦玉, 李鹏飞
基金资助:
国家自然科学基金(21963010); 国家自然科学基金(22061036)

Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes

Weina Tian^a, Liang Xu^a, Yu Wei^a(), Pengfei Li^b()

a State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003
b Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an 710054

Received:2023-01-02 Revised:2023-03-01 Published:2023-04-13
Contact: Yu Wei, Pengfei Li
Supported by:
National Natural Science Foundation of China(21963010); National Natural Science Foundation of China(22061036)

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摘要/Abstract

报道了一种N,O-螯合型B,B-二芳基四配位硼络合物的制备方法. 以稳定、易得的芳基氟硼酸钾(ArBF₃K)为二芳基硼(Ar₂B)结构单元的来源, 异喹啉-3-羧酸为N,O-螯合配体的前体, 在锰、对甲苯磺酰氯、碱存在下即可获得异喹啉- 3-羧酸根螯合的二芳基硼络合物. 该体系具有良好的底物适用性和官能团兼容性, 为合成二芳基硼络合物提供了一条便捷、高效的反应路径.

关键词: 四配位硼络合物, 异喹啉-3-羧酸, 芳基氟硼酸钾

A method for the preparation of N,O-chelated B,B-diaryl tetracoordinated organoboron complexes is disclosed. Using stable and readily available potassium aryltrifluoroborates (ArBF₃K) as the surrogate of the diarylboron (Ar₂B) moieties and isoquinoline-3-carboxylic acid as the precursor of the N,O-chelating ligand, the isoquinoline-3-carboxylate chelated diarylboron complexes can be obtained in the presence of Mn, p-toluenesulfonyl chloride, and base. This reaction is featured by broad substrate scope and functional group compatibility, thus providing a convenient and efficient pathway towards diarylboron complexes.

Key words: tetracoordinated organoboron, isoquinoline-3-carboxylic acid, potassium aryltrifluoroborate

引用此文

田维娜, 徐亮, 韦玉, 李鹏飞. 异喹啉-3-羧酸根螯合的B,B-二芳基四配位硼络合物的合成[J]. 有机化学, 2023, 43(5): 1792-1798.

Weina Tian, Liang Xu, Yu Wei, Pengfei Li. Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1792-1798.

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图/表 5

图式1. (a)四配位有机硼络合物典型结构、(b)传统合成二芳基硼型络合物的方法和(c)使用芳基氟硼酸钾引入(双)芳基硼结构单元的研究

Scheme 1. (a) General structure of the tetracoordinated organo- boron, (b) traditional synthetic methods for the preparation of B,B-diaryl complexes, and (c) disclosed methods to introduce (di)arylboryl moieties using ArBF3K

Entry	Variations from the standard conditions	Yield^b/%
1	None	80
2	Without Mn	N.R.^c
3	Without TsCl	N.R.^c
4	Without Na₂CO₃	60
5	TsCl (1.0 equiv.)	20
6	TsCl (2.0 equiv.)	50
7	Mn (4.0 equiv.)	20
8	DMF (2.0 mL) instead of CH₃CN (2.0 mL)	30
9	DMA (2.0 mL) instead of CH₃CN (2.0 mL)	40
10	DMSO (2.0 mL) instead of CH₃CN (2.0 mL)	N.R.^c
11	NMP (2.0 mL) instead of CH₃CN (2.0 mL)	20
12	80 ℃ instead of 130 ℃	10
13	110 ℃ instead of 130 ℃	44
14	2a (4.0 equiv.)	65
15	2a (3.0 equiv.)	27

表1. 生成四配位硼络合物3a的反应条件优化a

Table 1. Optimization of reaction conditions for the preparation of tetracoordinated organoboron 3a

表2. 四配位有机硼络合物的底物范围表a,b

Table 2. Substrate scope of the preparation of tetracoordinated organoboron compounds

图式2. 3a作为光催化剂的光氧化反应

Scheme 2. Application of 3a as the photocatalyst in photooxidation reactions

图式3. 可能的反应路径

Scheme 3. Proposed reaction pathway

参考文献 19

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异喹啉-3-羧酸根螯合的B,B-二芳基四配位硼络合物的合成

Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes

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