I<sub>2</sub>-Catalyzed Aerobic α,β-Dehydrogenation and Deamination of Tertiary Alkylamines: Highly Selective Synthesis of Polysubstituted Pyrimidines via Hidden Acyclic Enamines
Qinghe Gao, Manman Wu, Ke Zhang, Ning Yang, Mengting Liu, Juan Li, Lizhen Fang, Suping Bai, Yongtao Xu
Abstract
A novel and efficient entrance to the pyrimidine skeleton has been presented via the α,β-dehydrogenation and deamination of tertiary alkylamines. This I2-catalyzed dehydrogenative multicomponent procedure utilizes simple aldehydes to trap the hidden enamine intermediates and suspend generation of azadienes from amidines, enabling the difunctionalization of a vicinal C(sp3)–H bond. These studies provide valuable possibilities for the introduction of aliphatic substituents and show how to switch to a new reactive modality.
Topics & Concepts
ChemistryDehydrogenationEnamineDeaminationCatalysisCombinatorial chemistryHydroaminationPyrimidineOrganic chemistryMedicinal chemistryStereochemistryEnzymeCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAdvanced Synthetic Organic Chemistry