Recent Developments in Palladium-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles

This short review describes new developments in palladium-catalyzed aminoarylation reactions between aryl halides and alkenes bearing pendant nitrogen nucleophiles. These transformations provide a novel and powerful method for accessing numerous three-, five-, six-, and seven-membered nitrogen heterocycles. 1 Introduction 2 Synthesis of Pyrrolidines via Palladium-Catalyzed Alkene Aminoarylation Reactions 2.1 Palladium(0)-Catalyzed Alkene Aminoarylation Reactions 2.1.1 Synthesis of trans-2,5-Disubstituted Pyrrolidines 2.1.2 Transformations of Aryl Chloride Electrophiles 2.1.3 Synthesis of Hexahydro-3H-pyrrolizin-3-ones 2.1.4 Enantioselective Synthesis of Monosubstituted Pyrrolidines 2.1.5 Asymmetric Total Synthesis of (+)-Aphanorphine 2.2 Palladium(II)-Catalyzed Arene C-H Activation/Alkene Aminoarylation 3 Synthesis of Other Five-Membered Heterocycles via Palladium-Catalyzed Alkene Aminoarylation 3.1 Synthesis of Pyrazolidines 3.2 Synthesis of Isoxazolidines 4 Aminoarylation Reactions for the Synthesis of Three-, Six-, and Seven-Membered Heterocycles 4.1 Synthesis of Aziridines 4.2 Synthesis of Morpholines 4.3 Synthesis of Saturated 1,4-Benzodiazepines 5 Palladium-Catalyzed Synthesis of Fused-, Bridged-, and Spiro-Polycyclic Heterocycles 5.1 Cascade Alkene Difunctionalization Reactions 5.2 Tandem N-Arylation/ Alkene Aminoarylation Reactions 5.3 Intramolecular Alkene Aminoarylation Reactions 5.3.1 Synthesis of Tropane Derivatives 5.3.2 Synthesis of Spirooxindoles 5.3.3 Cascade C-H Functionalization/Intramolecular Alkene Aminoarylation Reactions 6 Conclusions