Base-Mediated Formal Denitrogenative Insertion of Nonactivated Triazoles into Aldehydes: Stereospecific Synthesis of Highly Substituted Acrylamides.
Teng L., Wang S., Zhu W., Dong X., Xiao T., Qin G., Anderson EA., Jiang Y.
A base-mediated denitrogenative insertion of nonactivated N(1)-aryl-1,2,3-triazoles into aldehydes to construct trisubstituted (E)-acrylamides was developed. The reaction, which involves formal insertion of two atoms from the triazole into the aldehyde C═O bond with concomitant loss of nitrogen, proceeds at ambient temperature with complete stereocontrol. This method provides a highly efficient and straightforward means to construct functionalized acrylamides by employing readily available 1,2,3-triazoles and aldehydes as starting materials.