Hydroxylamines as One-Atom Nitrogen Sources for Metal-Catalyzed Cycloadditions
Xinjun Luan, Jingxun Yu
Abstract
Abstract Transition-metal-catalyzed C–N bond formation is one of the most important pathways to synthesize N-heterocycles. Hydroxylamines can be transformed into a nucleophilic reagent to react with a carbon cation or coordinate with a transition metal; it can also become an electrophilic nitrogen source to react with arenes, alkenes, and alkynes. In this short review, the progress made on transition-metal-catalyzed cycloadditions with hydroxylamines as a nitrogen source is summarized. 1 Introduction 2 Cycloaddition To Form Aziridine Derivatives 2.1 Intramolecular Cycloaddition To Form Aziridine Derivatives 2.2 Intermolecular Cycloaddition To Form Aziridine Derivatives 3 Cycloaddition To Form Indole Derivatives 4 Cycloaddition To Form Other N-Heterocycles 4.1 Aza-Heck-Type Amination Reactions 4.2 Nitrene Insertion Amination Reactions 4.3 Intramolecular Nucleophilic and Electrophilic Amination Reactions 5 Conclusion and Outlook