Work

Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes

Year: 2020

Type: article

Abstract: The base-induced reaction of aryl diazonium salts with commercially available CF 3 SO 2 Na/CF 2 HSO 2 Na allows for the generation of the corresponding diazene radicals along with fluoromethyl radicals. The addition of fluoromethyl radicals to alkenes with subsequent diazene trapping provides the azofluoromethylation products in good to excellent yields. This metal-free method under mild reaction conditions has broad functional group compatibility and is applicable in the late-stage modification of various natural products and bioactive molecules.

Source: Organic Letters

DOI: 10.1021/acs.orglett.0c01395

Authors: Zhichao Lu, Olivia Hennis, Joseph Gentry, Bo Xu, Gerald B. Hammond

Institutions: University of Louisville, Williams College, Donghua University

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: National Natural Science Foundation of China, National Institute of General Medical Sciences

Awards: G4645608422, Nucleophilic halogenation reagents