Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature

doi:10.6023/cjoc202211033

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1815-1823.DOI: 10.6023/cjoc202211033 Previous Articles Next Articles

Special Issue: 有机硼化学专辑

ARTICLES

室温下电化学合成保护型有机硼酸RB(dan)

张俊颖, 赵晓静, 李干鹏^*(), 何永辉^*()

云南民族大学民族医药学院民族药资源化学教育部重点实验室民族药内生真菌天然产物生物合成国家民委重点实验室昆明 650500

收稿日期:2022-11-27 修回日期:2023-02-19 发布日期:2023-03-17
通讯作者: 李干鹏, 何永辉
基金资助:
国家自然科学基金(21662045); 国家自然科学基金(11547233); 云南省应用基础研究(202101AT070079)

Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature

Junying Zhang, Xiaojing Zhao, Ganpeng Li(), Yonghui He()

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650500

Received:2022-11-27 Revised:2023-02-19 Published:2023-03-17
Contact: Ganpeng Li, Yonghui He
Supported by:
National Natural Science Foundation of China(21662045); National Natural Science Foundation of China(11547233); Applied Basic Research Project of Yunnan Province(202101AT070079)

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Abstract

An electrochemical room-temperature synthesis of masked organoboronic acids RB(dan) (R=alkyl or aryl) has been developed. At room temperature, 1,8-diaminonaphthalene and boronic acids can smoothly participate in this reaction to provide a wide variety of RB(dan) (R=alkyl or aryl) in an undivided cell. The transformation has broad substrate scope and avoids using high-temperature or transition-metal catalysts, making it more sustainable and renewable.

Key words: electrochemical synthesis, boronic acids, masked group, room temperature

Cite this article

Junying Zhang, Xiaojing Zhao, Ganpeng Li, Yonghui He. Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1815-1823.

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Fig. & Tab. 7

References 36

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Entry	Variation from the standard condition	Yield^b/%
1	None	90
2	0.5 h instead of 1 h	80
3	2 h instead of 1 h	85
4	ⁿBu₄NClO₄ instead of LiClO₄	46
5	ⁿBu₄NBF₄ instead of LiClO₄	55
6	ⁿBu₄NI instead of NH₄I	68
7	No NH₄I	Trace
8	5.0 V instead of 5.5 V	67
9	4.0 V instead of 5.5 V	61
10	6.0 V instead of 5.5 V	51
11	10 mA in constant current	30
12	DMSO instead of MeCN	Trace
13	DMF instead of MeCN	n.r.
14	MeOH instead of MeCN	35
15	H₂O instead of MeCN	Trace
16	60 ℃ instead of r.t.	80
17	C(+)\|C(–) instead of Pt(+)\|Pt(–)	63
18	C(+)\|Pt(–) instead of Pt(+)\|Pt(–)	66
19	GF(+)\|Pt(–) instead of Pt(+)\|Pt(–)	81
20	No current	33
21	No Et₃N	62
22^c	Large-scale reaction	75

Entry	Variation from the standard condition	Yield^b/%
1	None	90
2	0.5 h instead of 1 h	80
3	2 h instead of 1 h	85
4	ⁿBu₄NClO₄ instead of LiClO₄	46
5	ⁿBu₄NBF₄ instead of LiClO₄	55
6	ⁿBu₄NI instead of NH₄I	68
7	No NH₄I	Trace
8	5.0 V instead of 5.5 V	67
9	4.0 V instead of 5.5 V	61
10	6.0 V instead of 5.5 V	51
11	10 mA in constant current	30
12	DMSO instead of MeCN	Trace
13	DMF instead of MeCN	n.r.
14	MeOH instead of MeCN	35
15	H₂O instead of MeCN	Trace
16	60 ℃ instead of r.t.	80
17	C(+)\|C(–) instead of Pt(+)\|Pt(–)	63
18	C(+)\|Pt(–) instead of Pt(+)\|Pt(–)	66
19	GF(+)\|Pt(–) instead of Pt(+)\|Pt(–)	81
20	No current	33
21	No Et₃N	62
22^c	Large-scale reaction	75

室温下电化学合成保护型有机硼酸RB(dan)

Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature

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