Abstract
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
Key words
alkenes - amines - arylation - catalysis - heterocycles - palladium - stereoselective
synthesis
