Photochemical Reductive Carboxylation of <i>N</i>-Benzoyl Imines with Oxalate Accelerated by Formation of EDA Complexes
Wenwen Liu, Pei Xu, Hui-Xian Jiang, Menglei Li, Tian-Zi Hao, Yiqin Liu, Songlei Zhu, Kun-Xiao Zhang, Xu Zhu
Abstract
Herein, a visible-light-induced umpolung strategy for reductive carboxylation of imines for synthesis of unnatural α-amino acids was disclosed. A reaction mechanism involving electron-donor–acceptor (EDA) complex formation between substrate and oxalate to furnish the desired products was proposed. Oxalic salt in situ generates CO 2 radical anion (CO 2 •– ) and carbon dioxide (CO 2 ) as the key single-electron reductant and carbonyl (C1) source, respectively, during the transformation with or without photocatalyst.
Topics & Concepts
CarboxylationOxalateChemistryCatalysisPhotochemistryReductive eliminationCombinatorial chemistryOrganic chemistryCarbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsFluorine in Organic Chemistry