Base-Mediated Amination of Alcohols Using Amidines
Chunyan Zhang, Zehua Li, Jianbin Chen, Shuo Qi, Yanchen Fang, Sheng Zhang, Chaoyu Ren, Fenghong Lu, Zuyu Liang, Shaohua Jiang, Xiaofei Jia, Shuangming Yu, Guoying Zhang
Abstract
Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.