Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides

doi:10.6023/cjoc202405009

Chinese Journal of Organic Chemistry Previous Articles Next Articles

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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^a, 陈龙徽^a, 王光伟^a,*

^a天津大学理学院,天津 30072

收稿日期:2024-05-09 修回日期:2024-05-31
基金资助:
国家自然科学基金(No. 22271214)资助项目.

Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides

Feifei Fan^a, Longhui Chen^a, Guangwei Wang^a,*

^aDepartment of Chemistry, School of Science, Tianjin University, Tianjin 300072

Received:2024-05-09 Revised:2024-05-31
Contact: * E-mail: wanggw@tju.edu.cn
Supported by:
Natural Science Foundation of China (No. 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. In this paper, we developed 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. 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

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Feifei Fan, Longhui Chen, Guangwei Wang. Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202405009.

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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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