Base-Promoted Tandem Synthesis of 2-Azaaryl Tetrahydroquinolines
Shuguang Chen, Langxuan Yang, Yongjia Shang, Jianyou Mao, Patrick J. Walsh
Abstract
A novel method to synthesize 2-azaaryl tetrahydroquinolines by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives is reported (over 30 examples, yields up to 95%). Mechanistic probe experiments demonstrate that the deprotonation of the benzylic C–H bond and the addition to the styrene vinyl group proceeds via the SNAr mechanism.
Topics & Concepts
ChemistryTandemDeprotonationStyreneNucleophilic aromatic substitutionCombinatorial chemistryBase (topology)StereochemistryOrganic chemistryNucleophilic substitutionPolymerIonCopolymerMathematical analysisMaterials scienceComposite materialMathematicsCatalytic C–H Functionalization MethodsChemical Synthesis and AnalysisSynthesis and Catalytic Reactions