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Issue 6, 2019
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Hydrogen bonding promoted simple and clean photo-induced reduction of C–X bond with isopropanol

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Abstract

We herein report a simple and clean photo-induced metal-free reduction of C–X bond under an atmosphere of air at room temperature. Isopropanol is used as both the reducing reagent and solvent. Various functional groups (acids, esters, alcohols, anilines, phenols, indoles, pyridines, cyano and trifluoromethyl groups) and other heterocyclic compounds are tolerated. Different organic halides (including C–I, C–Br and C–Cl bonds) can be dehalogenated with moderate to excellent yields. Polyhalides are also reduced chemoselectively and efficiently. DFT calculation suggests a six-membered ring transition state via C–X⋯H–O hydrogen bonding to decrease the activation energy.

Graphical abstract: Hydrogen bonding promoted simple and clean photo-induced reduction of C–X bond with isopropanol

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Publication details

The article was received on 10 Nov 2018, accepted on 19 Dec 2018 and first published on 20 Dec 2018


Article type: Communication
DOI: 10.1039/C8CC08942F
Citation: Chem. Commun., 2019,55, 767-770

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    Hydrogen bonding promoted simple and clean photo-induced reduction of C–X bond with isopropanol

    D. Cao, C. Yan, P. Zhou, H. Zeng and C. Li, Chem. Commun., 2019, 55, 767
    DOI: 10.1039/C8CC08942F

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