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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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Article information


Submitted
10 Nov 2018
Accepted
19 Dec 2018
First published
20 Dec 2018

Chem. Commun., 2019,55, 767-770
Article type
Communication

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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