The construction of C−N bonds of (hetero)aromatic compounds are manifestly important transformation in synthetic chemistry since it can offer nitrogen-containing molecules of great interest in biological, pharmaceutical, and materials sciences. During the past decades, remarkable progresses have been made in the metal-facilitated C−N bond forming-reactions such as hydroamination or oxidative amidation of double or triple bonds as well as the Buchwald-Hartwig type cross couplings. Despite these significant advances, direct installation of amino groups or their surrogates on aryl- or alkyl C-H bonds is still highly challenging.
In this poster, we will describe unprecedented Ag-mediated C−N bond formation of benzoxazoles by the decarbonylative coupling with formamides. On the basis of the mechanistic consideration, we also developed a direct amination protocol with parent amines under highly mild conditions.
During the study of catalytic system for this reaction, we found that catalytic amount of other transition metal (eg. Co, Mn) with peroxide instead of using stoichiometric silver were employed for this amination reaction. Further insight into the scope and mechanism of catalytic system are now under investigation.