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

doi:10.6023/cjoc202301001

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1792-1798.DOI: 10.6023/cjoc202301001 Previous Articles Next Articles

Special Issue: 有机硼化学专辑

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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

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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Abstract

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

Cite this article

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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References 19

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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

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

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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Fig. & Tab. 5

References 19

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