Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes

Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH3, R = H, Me), at room temperature without using catalysts and other reagents. This process is rapid and chemoselective, and features quantitative conversion and wide applicability for esters tolerating different functional groups. The experimental and theoretical studies reveal a reaction mechanism with nucleophilic addition followed by a swift proton transfer-induced elimination reaction. Amides are important organic compounds that are widely applied in medicine, biochemistry, and materials science. Here, the authors report a method for synthesis of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH3, R = H, Me), at room temperature without the use of catalysts.

Automated summary

Amides, important organic compounds widely used in medicine, biochemistry, and materials science, can be efficiently synthesized through a direct amidation of esters with sodium amidoboranes without the need for catalysts. This method is rapid, chemoselective, and features wide applicability for esters tolerating different functional groups.