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Copper Catalyzed Cyanation Of Aromatic Boronic Acids/Esters

Posted on:2013-03-08Degree:MasterType:Thesis
Country:ChinaCandidate:Y YeFull Text:PDF
GTID:2231330371997027Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Aryl nitriles are an important class of compounds. In organic chemistry, they are of substantial interest as integral ingredients of pharmaceuticals. natural products, dyes and herbicides. In addition, nitriles are valuable precursors in organic synthesis because they can be easily converted into an array of functional groups such as acids, aldehydes, amides and amines. However, traditional methods for the preparation of benzonitriles require harsh reaction conditions or the use of noble transition metals.Herein, we developed a method for the efficient and reliable synthesis of aryl nitriles via the Cu2O-catalyzed cross-coupling of aryl boronic acids or esters and TMSCN. A broad range of substrates decorated by electron-rich and deficient, sterically very congested, and labile functional groups were tolerated. Moreover, the reaction can be proceeded under mild conditions at room temperature. These advantages paired with the use of cheap, readily available, and halogen-free CU2O as catalysts make the protocol an appealing option for aryl cyanations.
Keywords/Search Tags:Copper, Trimethylsilylcyanide, Cyanation, Boronic acids, Boronic esters
PDF Full Text Request
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