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Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

ABSTRACT: The base-induced reaction of aryl diazonium salts with commercially available CF₃SO₂Na/CF₂HSO₂Na 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.

SUBMITTER: Lu Z

PROVIDER: S-EPMC7328341 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

Lu Zhichao Z Hennis Olivia O Gentry Joseph J Xu Bo B Hammond Gerald B GB

Organic letters 20200513 11

The base-induced reaction of aryl diazonium salts with commercially available CF3SO2Na/CF2HSO2Na 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 appli ...[more]

PMID: 32400165

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