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Oxidative radical addition–chlorination of alkenes to access 1,1-dichloroalkanes from simple reagents

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Abstract

The oxidative radical addition of alkenes has been achieved using a simple chlorine source in the presence of tert-butyl hydroperoxide under mild conditions. A series of anti-Markovnikov aryl chlorides were obtained in good to excellent yields with a broad substrate scope. Notably, the dichloroaryl compounds were successfully obtained under metal-free conditions, providing an easy method for the direct preparation of 1,1-dichloroalkanes. Furthermore, these reactions were performed in an open flask without inert gas protection, which is favorable for the future scale-up of this synthetic process. The mechanistic study suggested the involvement of a radical pathway.

Graphical abstract: Oxidative radical addition–chlorination of alkenes to access 1,1-dichloroalkanes from simple reagents

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Publication details

The article was received on 20 Mar 2019, accepted on 29 Apr 2019 and first published on 30 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00400A
Org. Chem. Front., 2019, Advance Article

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    Oxidative radical addition–chlorination of alkenes to access 1,1-dichloroalkanes from simple reagents

    C. Chen, Y. Li, Y. Pan, L. Duan and W. Liu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00400A

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