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Synfacts 2014; 10(12): 1316
DOI: 10.1055/s-0034-1379414
DOI: 10.1055/s-0034-1379414
Metal-Mediated Synthesis
Reaction of Arylboronic Acids with α-Aminoesters and α-Aminoacetonitriles
Wu G, Deng Y, Wu C, Zhang Y, Wang J * Peking University, Beijing and State Key Laboratory of Organometallic Chemistry, Shanghai,
P. R. of China
Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Aminoesters and α-Aminoacetonitriles with Arylboronic Acids.
Angew. Chem. Int. Ed. 2014;
53: 10510-10514
Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Aminoesters and α-Aminoacetonitriles with Arylboronic Acids.
Angew. Chem. Int. Ed. 2014;
53: 10510-10514
Further Information
Publication History
Publication Date:
18 November 2014 (online)
Significance
Wang and co-workers report a deaminative coupling of α-aminoesters and α-aminoacetonitriles with aryl boronic acids to yield α-aryl esters and nitriles. The reaction shows broad substrate scope and an excellent functional group tolerance.
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Comment
Electron-withdrawing substituents on the aryl boronic acid promote the reaction as they facilitate the coordination of the electron-rich diazo carbon atom to the electron-deficient boron center.
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