Chinese Journal of Organic Chemistry >
Tetrahydroxydiboron and Copper Sulfate Co-Promoted Facile Synthesis of Phthalides
Received date: 2024-05-09
Revised date: 2024-05-31
Online published: 2024-07-15
Supported by
National Natural Science Foundation of China(22271214)
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.
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 . DOI: 10.6023/cjoc202405009
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