Intermolecular Hydrazinative Halogenation of Alkenes with Potassium Halides as Nucleophilic Halogen Sources: Modular Entry to Phenelzine Derivatives

• DOI: 10.1021/acs.orglett.3c02475
• Publication Date: 2023-08-24T17:45:48Z
• Authors: Nan Huang; Lihao Liao; Xiaodan Zhao

An approach for the efficient synthesis of halogenated hydrazines via acid-mediated electrophilic hydrazinative halogenation of alkenes is disclosed. This transformation proceeds with readily available diethyl azodicarboxylate as a hydrazine source and low-cost potassium halides as nucleophilic halogen sources. A series of iodinated, brominated, and chlorinated hydrazines are facilely produced with a wide range of functional groups. The obtained products are good platform molecules. They can be conveniently converted into a variety of valuable phenelzine analogues which are appealing for development of novel drugs treating depression.