Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides

doi:10.6023/cjoc202405009

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3467-3475.DOI: 10.6023/cjoc202405009 Previous Articles Next Articles

ARTICLE

四羟基二硼和硫酸铜共同促进的苯酞类化合物的简便合成

范飞飞, 陈龙徽, 王光伟^*()

天津大学理学院化学系天津 300072

收稿日期:2024-05-09 修回日期:2024-05-31 发布日期:2024-06-07
基金资助:
国家自然科学基金(22271214)

Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides

Feifei Fan, Longhui Chen, Guangwei Wang^*()

Department of Chemistry, School of Science, Tianjin University, Tianjin 300072

Received:2024-05-09 Revised:2024-05-31 Published:2024-06-07
Contact: *E-mail:wanggw@tju.edu.cn
Supported by:
National Natural Science Foundation of China(22271214)

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Abstract

Transition-metal catalyzed cross-coupling is one of the basic strategies for the C—C bond formation. However, it is difficult to achieve satisfactory results when terminal alkynes with electron-withdrawing group such as propiolate esters are used. The reason behind this might be the easy polymerization of this type of alkynes in the presence of base. A tetrahydroxydiboron and copper sulfate co-promoted cross-coupling/cyclization of propiolate esters and o-iodobenzoic acid for the facile and efficient construction of phthalides is described. Preliminary mechanism study indicates that tetrahydroxydiboron can inhibit the polymerization of propiolate esters and increase the reaction rate. This method is characterized by high regio- and stereoselectivities, mild reaction conditions, short reaction time, broad substrate scope, and excellent functional group compatibility.

Key words: tetrahydroxydiboron, phthalides, copper sulfate, o-iodobenzoic acid, propiolate ester

Cite this article

Feifei Fan, Longhui Chen, Guangwei Wang. Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3467-3475.

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Fig. & Tab. 6

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Entry	Variation from the standard conditions	Yield^b/%
1	None	91 (86)
2	Add nahco₃ (2.0 equiv.)	81
3	Add Cs₂CO₃ (2.0 equiv.)	33
4	No B₂(OH)₄	25
5	Zn instead of B₂(OH)₄	40
6	Vitamin C instead of B₂(OH)₄	57
7	B₂pin₂ instead of B₂(OH)₄	35
8	B(OH)₃ instead of B₂(OH)₄	4
9	DMF instead of DMSO	67
10	Acetonitrile instead of DMSO	N.D.
11	80 ℃ instead of 40 ℃	22
12	Cu(OAc)₂H₂O instread of CuSO₄	77
13^c	CuCl₂ instead of CuSO₄	N.D.
14^c	CuI instead of CuSO₄	23
15^c	CuI instead of both CuSO₄ and B₂(OH)₄	64
16	CuSO₄5H₂O instead of CuSO₄	88 (86)
17	Add NaCl (3.0 equiv.)	13

Entry	Variation from the standard conditions	Yield^b/%
1	None	91 (86)
2	Add nahco₃ (2.0 equiv.)	81
3	Add Cs₂CO₃ (2.0 equiv.)	33
4	No B₂(OH)₄	25
5	Zn instead of B₂(OH)₄	40
6	Vitamin C instead of B₂(OH)₄	57
7	B₂pin₂ instead of B₂(OH)₄	35
8	B(OH)₃ instead of B₂(OH)₄	4
9	DMF instead of DMSO	67
10	Acetonitrile instead of DMSO	N.D.
11	80 ℃ instead of 40 ℃	22
12	Cu(OAc)₂H₂O instread of CuSO₄	77
13^c	CuCl₂ instead of CuSO₄	N.D.
14^c	CuI instead of CuSO₄	23
15^c	CuI instead of both CuSO₄ and B₂(OH)₄	64
16	CuSO₄5H₂O instead of CuSO₄	88 (86)
17	Add NaCl (3.0 equiv.)	13

四羟基二硼和硫酸铜共同促进的苯酞类化合物的简便合成

Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides

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References 40

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[3]	LIU HUIYING;YANG DAYU. Microdetermination of tin in organotin compounds [J]. Chin. J. Org. Chem., 1990, 10(2): 191-192.